


Kink Challenge Collection- Oswald Cobblepot

by JokesterWrites



Category: Gotham (TV)
Genre: F/M, JokesterWritesKink
Language: English
Status: In-Progress
Published: 2016-02-10
Updated: 2016-10-13
Packaged: 2018-05-19 14:42:44
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 29
Words: 30,606
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5970756
Author URL: https://archiveofourown.org/users/JokesterWrites/pseuds/JokesterWrites
Summary: <blockquote class="userstuff">
              <p>From my Tumblr Kink Challenge List</p><p>Each chapter is a separate one shot and not related to previous or future chapters.</p>
            </blockquote>





	1. Punishment (Spanking)

**Author's Note:**

> catching the other masturbating, spanking, dirty talk.

It was late at night and Oswald still hadn’t come to bed. You were feeling sexually frustrated. Every single intimate moment you’d had together as of late, had been interrupted and the whole week he had spent teasing you relentlessly. Sneaking hands along the inside of your thigh during dinner or worse yet, when he had slowly stroked your folds under the table, fingers teasing your entrance during a business meeting. You were desperate for release, your thighs clenched together in an attempt to either satisfy or quell your desires in public. Oswald had spent the entire afternoon whispering about all the dirty things he wanted to do to you, while the pair of you looked over reports in his meeting hall. He’d left you aroused and wanting to drag him off in private. Instead, he’d dismissed you after dinner. Oswald had another meeting with Jim Gordan.

Deciding that enough was enough, you stroked yourself outside your panties, feeling the silken fabric begin to soak with your juices. Tugging a pillow between your legs you humped it, grateful for the beginning build of friction. Your hand reached down, fingers dipping inside, teasing your clit.

You breathlessly panted, eyes closed re-imagining his exact words from this afternoon. How he would bend you over his knee and finger fuck you into oblivion. “Oswald!” you moaned out.

“Yes?”

Your eyes shot open and your body stilled. Oswald was leaning against the doorway, watching you with a dangerous smirk on his lips. Embarrassed you quickly pulled your hand out of your panties and tugged the pillow away, drawing your knees up to your chin defensively.

“I see you’re being a naughty girl. Couldn’t wait for me? What a wanton little slut you are.” He stepped into the bedroom, limp prominent as he stalked towards you, shedding his suit jacket before sitting on the edge of the bed. He knew how wet you would get just at his voice uttering those filthy words. You bit your lip when he reached to feel how soaked your panties were,“Very naughty I see. I think I’ll have to punish you for this.” Oswald’s face was stern, a shadow of a smile ghosting over his features.

“Yes please,” You breathed, remembering his earlier words.

He adjusted himself on the bed and patted his knee, “Come here,” he commanded, his eyes following your every move as you draped yourself over his knees.

A shudder of pleasure washed over you as he slipped your panties off to caress the curve of your bum. Then his hand brought down in a sharp smack, leaving a pink blush behind. You yelped at the sting of his hand, not quite expecting Oswald to pin you down and spank you.

“My poor little dove.” He cooed, caressing the warm skin of your cheeks. Your face flushed with excitement and a tinge of humiliation as he slid his fingers between your legs, testing how aroused you were. “Such a wanton minx you must be. So needy and wet. You were probably cumming from my words alone this afternoon.” He brought his hand down against your ass again. You moaned a bit at the sharp feeling. “Oh god yes. Again, please.” You whispered.

Oswald smirked, “Count them, hussy.” he demanded, striking your skin over and over again. “Is that all you are? A painted whore? Should I fuck your pretty little demon’s purse?”

“Please!” Tears pricked at the corners of your eyes and soft moaning sobs broke out as you counted each time his hand made contact with your stinging bum. You could feel his erection digging in underneath you, and you desperately wanted him.

Finally he stopped and pulled you up.”:Get on all fours.” He demanded, his fingers making quick work of opening his pants and letting his erection spring out. You were quick to settle yourself on the bed, eager for his cock to fill you. He clasped your hips and thrust in. A gasp escaped you at the sensation of the fabric of his pants brushing your sensitive skin with every hard thrust he gave.

“Fucking slut. Do you want my cock buried deep in you? I’ll fuck your pussy so hard you won’t be able to sit.” Oswald’s profanity spurred your begging moans on. “Everyone will know what a hussy you are. Scream my name.” He swore at you. 

“Penguin, please! Fuck!” You could barely string a words together to make a coherent thought while he was ramming into you. The use of his moniker only encouraged his quick thrusts, and Oswald drew back a hand to slap your ass again. Your orgasm washed over you in ripples, your cunt tightening around his cock.

“Fuck!” He grunted, giving one last hard thrust to spill his seed before he collapsed against you. Breathing heavily he rolled off and gathered you into his arms, kiss along your face where there were still traces of salty tears from his earlier administrations.

“I love you so much.” He reminded you over and over again between each adoring kiss. Feeling sore, but infinitely satisfied you cuddled into him. “I love you too darling.”


	2. Heavy Petting (Bush/First Time)

**Notes for the Chapter:**

> First time, bush

Dating Oswald was perfection. He was the ultimate gentleman and you couldn’t imagine having anyone else for your first boyfriend. Though he often insisted on taking you out on extravagant dates, tonight was a relaxing evening. Oswald had a chef come in and cook a lovely dinner. After dinner you snuggled together on the couch to watch a movie in the dim light of the living room. Oswald carefully rearranged himself behind you in a spooning position, his arm respectively placed over your stomach.

As the evening wore on, Oswald’s breathing became slightly shorter as a particularly steamy sex scene came on screen. Feeling dampness pool between your legs, you shifted and stretched, your bottom accidentally grazed into Oswald’s crotch. You froze, feeling something hard press back. Did he have a boner? Curiosity got the better of you and you faked another stretch, pressing back more firmly and circling your hips.

Oswald let out a soft moan and then his lips were brushing along the line of your neck, sucking at the sensitive skin. His arm tightened around your waist, drawing you closer as he ground his hard on into the curve of your ass. Oswald adjusted, lying you beside him as his hand stroked under your blouse, caressing the bare skin, before he moved on, massaging your center over your jeans as he claimed your lips with his own.

Everything felt wonderfully blissful. You hadn’t experienced anything like this before, especially the pooling want where he pleasured you through the rough texture of jeans. Then Oswald’s hand moved upwards, fingering the button of your pants and then your hands were on his. “Wait!”

Oswald’s eyes were focused on you in a second, a mix of hunger and confusion. “What’s wrong?”

You flushed, slightly embarrassed at your inexperience and a nawing worry that he wouldn’t like what he found. Despite having seen enough television to know that woman waxed their intimate areas bare, you hadn’t ever groomed your own garden. Mostly on the belief that no one would see it. Yet now Oswald was asking entrance at this very moment.

“I just… I’ve never…” It felt awkward trying to explain your virginity.

Oswald instantly understood, hushing your concerns. “It’s okay. I’ll stop if you want.” There was a tenderness to him and you instantly shook your head, “No… I want to. This feel right.”

His fingers fumbled with your jeans again, popping the button open. Distracting you with more kisses, Oswald delved in, rubbing his fingers over the silkiness of your panties, testing the dampness of them. The friction felt wonderful, and you arched into him, forgetting about everything with the feel of his hands on you. Then Oswald was between your legs, drawing away the jeans and tossing them to the floor.

He could still sense your tenseness as he drew your panties down, revealing the soft curls nestled between your legs. Oswald could see the droplets of juices collecting there and he let out a groan. There was a tightness in your chest that eased as Oswald’s appreciation for your personal garden was verbalized and then acted upon. You were about to protest as he kissed up the inside of your thighs, teasing your skin, but then he licked one long stripe up your folds and that protest died on your lips. It felt too wonderful as Oswald teased and ate you out. You came with a cry, gushing and Oswald diligently licked away the evidence of your pleasure. He worked on you again, building up the tight knot and bringing you crashing into another orgasm. Your thighs were quivering around him and Oswald smirked, pleased at your reaction.

“You are so beautiful.” Oswald murmured, crawling his way up your body and helping you remove your blouse and bra. Thumbs ran over your already perked nipples and you dragged him down into an erratic kiss. Oswald pulled away to shuffle off his own clothes, wanting to feel your skin against his. Your eyes were instantly on his erection, as he rolled a condom on. How was that supposed to fit?!

Your hesitation was evident and Oswald soothed away your fears, providing further pleasure to your skin with soft kisses and little nibbles. Then his fingers pushed into you and you squirmed. It was a foreign feeling, but it slowly built into a pleasurable one as he gently worked you, stretching your walls in preparation for his cock.

“Is this okay?” Oswald asked softly, looking into your eyes for permission as he withdrew his fingers and rubbed his cock as your entrance, coating the head with your juices. There was a nervous zing of energy as you quickly nodded. Oswald pressed in slowly, and you shifted, feeling a moderation of discomfort as he filled you. There was a elongated pause as Oswald stilled his hips, waiting for you to adjust to this new feeling. The kisses he placed on your lips, coaxing your mouth open as his hands stroked soothingly along your arms. Then he was moving, slowly paced thrusts into you. He pulled your legs over his hips, encouraging you to hook them behind his back, drawing him in. The discomfort faded away and bloomed into pleasure as Oswald rocked into you. His grunts marked each thrust and then suddenly he shuddered, eyes closed as a long groan of pleasure rolled off his tongue. “Fuck.” He swore, a hazy bliss marking his eyes when he opened them to gaze down at you underneath him. Then he pulled out, discarding the condom before drawing you into his arms, giving lazy kisses as he tugged a blanket overtop of the pair of you. 

You felt tired, sore and in need of a hot bath when you woke later, but there was a sated feeling of satisfaction as you glanced over at Oswald’s sleeping form. His soft breaths tickled the back of your neck and even in sleep he held you tightly.


	3. Three's a Charm (Skype Sex)

**Notes for the Chapter:**

> Kink Challenge Request #32:Skype/web cam sex (REQUESTED) +57,69 OswaldxReaderxHooker  
> “ Oswald hasn’t been able to see his girlfriend so they video chat. And one of his kinks is watching his girlfriend with another girl. “

“Is this working?” You adjusted the webcam attached to the screen of your laptop. “Dear god… what are you wearing?” You eyed the yellow shirt and grey sweater skeptically. 

Oswald grinned as your face came into view. “It’s working,” He ignored your comment about his clothes, “I’ve missed you.” He adjusted his laptop on the table of the trailer,making sure that the tied up man wouldn’t be visible or audible during your call.. He’s been pleased to find out that the rich boy had a laptop with him in the truck, it even included with a built in webcamera. He’d eyed the Porn folder on it with mild interest, but instead he’d called you to assuage any worries… and perhaps make a few suggestions for when you called him.

You made a face, “Well whose fault is that? You decided to rat out Fish.” Leaning out of the camera’s immediate viewpoint, it showed off your bed.

“I’d rather not talk about my mistakes right now.” He muttered, “Besides, I thought we agreed you’d have a surprise for me?” He could hear some light shuffling off camera and adjusted his position, unbuckling his pants in preparation of the show to come.

“You don’t deserve this surprise…” You called out to him, quickly shucking off your clothes.

His eyes widened when you came back into view, another woman with you. “Excellent..” He breathed, already eager to start. A small whimper came from across from him and his eyes shot up to connect with his captive. They narrowed and the man visibly paled and he shuffled deeper against the wall.

Oswald turned his attention back to his girlfriend and her plaything. He licked his lips, hungry to watch you. His hand encircled the girth of his cock, and he languidly stroked it.

You reclined against the bed, already having figured out the best angle for Oswald to watch the pair of you at. The hooker you’d hired was pretty, all soft curves. She moved between your legs, kissing her way up your body, finding the little spots that made you moan in pleasure. She kissed you, her tongue battling with yours and you ran your hands across her skin, urging her on. Your body began to beg for friction between your legs and you rolled your hips against her thigh. She smirked and ran her fingernails along you body, eliciting little cries of pleasure until she pushed a finger into your tight heat. She watched your face for signals of what was turning you into a puddle of goo at her touch. 

Her tongue followed her fingers and she knelt between your thighs, making quick work of bringing you to the brink and back again. Your lust filled eyes drifted past where she was eating you out to the laptop. You could see Oswald’s breathless face and the tilt of his shoulder as he fisted his cock furiously in time to the hooker’s attentions.

“Faster.” You begged, arching off the bed. She followed your request and it pushed you over the edge. You fell back crying out Oswald’s name.

“Fuck.” He cursed and gave a few more hard tugs before spilling onto his hand.

The hooker got up and tugged her dress on, rifling through the roll of bills you’d placed on the counter. “Thanks,” She mentioned before leaving, closing the door with a soft click behind her.

Relaxed you shifted on the bed, coming closer to the camera. “Well Os… I should really be punishing you for not being here to partake… promise me you’ll come home soon? She was pretty good.”

He nodded, “I’ve got a few things to sort out before I come back. But I will come back.” Oswald gave you a brief smile and studied you once more, burning your naked beauty into his mind. He knew he couldn’t risk too many of these calls. Not when there was work to be done. Gotham was his home and he was going to return to rule it.


	4. Chauffeur (Road Head)

**Notes for the Chapter:**

> Kink Request- Road Head

As Oswald’s personal chauffeur you were used to waiting for him during his meetings. Today however, the wait was short and Oswald slammed the door shut behind him as he slid into the passenger’s seat. ‘Drive.” He snapped, crossing his arms in irritation.

Used to the brusque manner of your boss, you pulled the car out, taking the long scenic route that he preferred when he was brooding. It was midday in autumn, the leaves changing colours and drifting down as you drove.

“Stop. Pull over here.”

Oswald’s words were quiet, dangerously demanding in their soft quality. Drawing the car to the side of the road, it idled as you waited for Oswald’s next request. There was a deadening silence between you as Oswald stewed, a petty expression smeared across his face as he watched cars go by.

“Well, turn it off!” Oswald growled, tugging at his cravat and opening the top buttons of his shirt. His posture was tight, eyes flickering, jaw tensing and grinding with suppressed anger. “Is there something I can do to help you relax Mr. Cobblepot?” You asked tentatively, not wanting to overstep your boundaries as you cut the power to the engine with a flick of the key.

His eyes were drawn to your hand on the stick shift, where it was subconsciously caressing the leather knob. “Service me.” He said suddenly, staring you down with an intensity as his leather gloved hand caressed the top of yours.

Your mouth felt suddenly dry and your fantasy was now tangible. It had crossed your mind before. Mr. Cobblepot was a unconventionally attractive man and his hands had been a point of fascination in your fantasies. Unbuckling your seatbelt, you adjusted and leaned over. Oswald was already unbuckling his pants, pushing them down, and drawing his half hard cock out. Eagerly you wet your lips and licked up his length, teasing the velvety head with your tongue.

“That’s my girl.” Oswald murmured, sliding your driver’s cap off and tossing it into the back seat. He caressed a hand through your hair, gripping the back of your neck and guiding you down on his cock with a groan. The obscene sounds of your mouth working him faster egged Oswald’s groans. He couldn’t get enough of the way your eyes looked up at him daringly, the excess spittle running down the side of your mouth. “Fuck” He cursed, closing his eyes as you caressed his balls, rolling them between your fingers. “Keeping going.”

You slurped along his shaft, the precum salty in the back of your throat as you took more of him into your mouth. Oswald applied pressure and thrust in, hitting the back of your throat causing you to gag around him. “Ahhh…” Oswald sighed happily, leaning his head back against the headrest.

“Stay down.” He said suddenly, his hand firm on your head. Oswald’s eyes traced the GCPD cruiser as it passed by slowly. Your jaw was beginning to ache as he held you down, the hollowing of your cheeks marking the suction of your lips around his cock. With the cruiser gone, he let you up and you swallowed the excess saliva, licking your lips before ducking your head and taking his balls into your mouth. Hand fisting firmly along his dick, you pleasured him, enjoying the small grunts and puffs of air as Oswald came close to his peak.

“I’m almost there.” He warned hoarsely. You returned to his shaft, stimulating the head with your swirling tongue again. Then he was cumming, salty spurts filling your mouth and sliding down his erection. Slurping them up, you took care to lick him clean as Oswald stroked those soft leather gloves along the side of your face, a look of satisfaction across his face.

“Thank you, my dear.” Oswald murmured, far more relaxed and at ease now. The tension was smoothed from his shoulders, and the charming light was back in his eyes. You smiled as he straightened his suit out, your back giving a satisfying pop as you straightened back into your seat. “You’re welcome, sir. Anytime.”

Oswald gave you an appreciative look. “I may have to request a private drive more often then…”


	5. Adoration (i love you)

**Notes for the Chapter:**

> Kink Request; I love you

“Os, which one do you think I should wear?” You turned to him, holding up two dresses. One was black and lace, while the other was a dark blue satin.

He studied both of them for a moment, and then walked up to you. He took the dressed from you, and gave each a secondary cursory glance before shrugging and throwing them over his shoulder to land in a crumpled pile on the floor of your bedroom. “Oswald!” You scolded him. He simply smirked and drew you into his arms. “I prefer this.” He murmured into your ear, hot breath brushing along your neck. His nimble fingers tugged at the drawstring keeping your robe closed, and he bent down to bury his face in your breasts. “We have a dinner to go to!” You protested with laughter. “Mmmm I know… I’m having the first course now.” He teased, nibbling at your nipples through the sheer brassiere.

You smacked his shoulder. “Oswald Chesterfield Cobblepot. Stop being a caveman and help me dress.”

“That’s no fun my dear, I’d rather help you undress.” He reached behind you to unsnap your bra, drawing both it and your robe off your shoulders. Giggling, you helped by slipping off your panties. Oswald backed you onto the bed, shedding his clothes as he stalked you.

Pressing you back into the mattress he kissed you. There were time he couldn’t believe that he had such a beautiful woman who cared for him unconditionally. You were perfection. He adored you, but was also afraid of saying that he loved you. What if you changed your mind?

He pressed between your legs, pushing in gently. Oswald wanted to take you slow and sweet. He wanted to cherish every tremor that went through your body. He worshipped you, kissing every inch of skin he could reach, murmuring how beautiful, how smart, how incredible he found you. He drew every moan out of your body with satisfaction, until you came apart in his arms. He watched your face drown in bliss as each wave of pleasure rained over you. He didn’t last too much longer, not with your sweet cunt tightening around him, milking him for all he was worth. A strangled sound escaped his lips and he collapsed next to you.

A knock on the door startled the pair of you. “Penguin, sir. The car is ready.”

You giggled, and slide a leg around Oswald’s, effectively holding him in place. “Why don’t we stay in?” You suggested, snuggling into him.

Oswald agreed. He untangled himself and grabbed his elaborate robe to answer the door. He opened it enough to give orders before closing and locking it. “Now where were we?” Oswald mused, raising an eyebrow at you.  
“I believe we were snuggling in post orgasmic bliss.” You smiled at him, inviting him back into bed. He joined you under the covers, again marveling at how perfect you were for him. Oswald encircled his arms around you and hitched one of your legs across his hips. He wanted to be enraptured by you, covered in your loveliness again. Your fingers were tracing lazy circles on his chest and he hugged you close to kiss your forehead.

“I love you.”

It slipped out, completely unintentional and Oswald froze upon realizing what he had said.

You made a content sound, and kissed him comfortably. “I know.”

He stuttered, “You did?”

Shrugging, you shifted so you could look at him properly. “Yes. You did just put off dinner in favour of dragging me to bed. I’m not sure how else you could truly show how much you love me.” You teased him. “Irregardless… I love you, my Mr. Cobbelpot.”

A warm fuzzy feeling spread through Oswald. You loved him. A smile spread over his face, and he held you close, hand stroking over you skin in content bliss. He now had everything he ever wanted. Gotham. You. It was perfect.


	6. Enticing (Bathroom sex)

**Notes for the Chapter:**

> #55-in a really dirty place (like a public toilet) OswaldxReader

Oswald took you out to the most expensive restaurant in Gotham for a special dinner. It was an apology of sorts for being so busy as of late. He felt like he was neglecting you.Sometimes he found it difficult to balance his work life with his personal life, especially because he never wanted them to intertwine. Like his mother, he tried to keep you far away from his unsavory business.

“This is wonderful Oswald.” You gushed, admiring the beautiful restaurant that overlooked the canal and the lit city beyond.

Oswald beamed, a warm tingly feeling filling his body at your happiness. He pulled out your chair for you and then took his own seat. “I took the liberty of ordering our usual.” He admitted, “Then we wouldn’t have to wait very long… I’ve been looking forward to a lovely evening alone with you.”

Your eyes sparkled mischievously, “Sounds enticing…..” You leaned you head against your hand, and let your foot slide out of your shoe and trail delicately up his leg. Oswald made an odd tittering sound when you reached the inside of his thigh. He gulped some wine down, choking on it a bit when you stretched to rub against his crotch.

“Are you feeling alright Os?” You asked innocently, taking a delicate sip of your own wine.

“Perfectly fine. Just… had an inspiring thought.” He replied, shifting in his seat. You tilted your head, “Mmm… me too…Do you think they’ll hold the table while I nip out to powder my nose?” You gave Oswald a suggestive look.

His eyes gleamed, “I can guarantee it. Would you care for an escort?”

“Certainly. One never knows what can happen between a table and a ladies room.” You collected your clutch and stood up, “But perhaps you best wait a few moments.”

Oswald smirked. He waited a few minutes and finished his drink before making is way towards the restrooms. Glancing around he made sure no one was watching when he ducked into the ladies room. You were waiting for him, touching up your makeup in the mirror. Grinning he hobbled over and took your face in his hands to kiss you. Hungry for more you pushed him back, stumbling into the handicap stall and locking the door. Your frantic fingers made quick work of the buttons of his waist coat and you tugged his shirt from the black trousers. He was busy running his hands down your figure, sliding nimble fingers to slip off your panties and tucking them into his pocket.

“God what you do to me, mon cherie.” Oswald moaned against your skin. He spun you around, “Brace the bar.” He commanded. You leaned over. grasping the bar and spreading your legs. Oswald jiggled his pants open and then his attention snapped towards the door. Based off the sound, a pair of women had entered the bathroom, giggling and gossiping about their dinner partners. You glanced back at him questioning what he was going to do.

Oswald merely smirked and held a finger to his lips before positioning himself behind you and thrusting in. You bit your lip to hold back a moan at the feeling of fullness. He braced one hand on your shoulder, with the other on you hip to guide him. A grunt escaped his lips, and he paused in his administrations when one of the women called out, “Are you okay in there darling?”

Resisting the urge to giggle you replied, “Oh just fine. Ate some bad… seafood… I think.” Oswald bit his lip and slowly continued his thrusts, waiting for the women to leave.

A toilet flushed and he sped up his paces, letting the flushing water mask the sound of flesh slapping against flesh. He forced himself to slow again, making short quick pushes into you. You arched your back, gripping the bar with white knuckles as the head of his penis brushed against your sweet spot. Quickly you reached behind you to grasp his hand and drag it to the front, silently urging him. He quickly understood and began to stimulate your clitoris with his fingers. “So close” You whispered jaggedly.

“I know darling,” He replied, kissing the skin of your shoulder. “Just a few more.” You could feel your body tightening, and then the sweet rush of release flooded over you and you cried out. Oswald quickly gripped his hand around your mouth to stifle it. Eagerly you licked at his fingers, tasting your essence on them. Oswald’s eyes nearly rolled into the back of his head. He loved it when you acted so wanton with him.

Pushing him back and out of you, you popped the toilet seat cover down and Oswald sat on it, pants around his ankles. You quickly sunk down onto him, intent on riding him to his orgasm. It didn’t take long with you swirling your hips around him, he shuddered and let out a staggering moan with his eyes closed and head falling forward to your shoulder. He gently kissed your dewy skin, dragging his lips over you skin as he blinked back into reality. “Dinner is probably ready by now.” You clambered off him and fixed your skirt again before helping Oswald straighten out his suit.

He kiss you hungrily before leaving the bathroom. “I’m not sure I’m hungry for food anymore, my dirty little dove.”


	7. Hurricanes (Angry sex)

**Notes for the Chapter:**

> Kink Challenge #61-Dom/Sub (kind of) also #79 (calming others anger with sex)

Oswald felt a turmoil of emotions running through him. He’d just killed one of the candidates for mayor. Splatters of her blood still felt warm on his face. There was a tightness curling in his chest. He’d been selfish, damning a child to a motherless life for the sake of his own.

“Take me home, Butch.” Oswald commanded quietly. There was plenty to think about on the drive home. He had to find his mother. Dismissing Butch once they reached the mansion, Oswald paused on his way in, taking a long glance at the additional black car loitering in the driveway. “Who are you waiting for?” He questioned the driver standing beside it. The man looked down his nose at him, and Oswald’s anger bubbled close to the surface.

“I am waiting for Ms. ________________.” He stated, “Mr. Galavan has requested her presence at a Charity Ball this evening.”

Oswald felt chilled. No. Not his love too. They already had taken his mother. How dare Galavan so blatantly flaunt his power over Oswald like this.

“You can leave. “ Oswald had to think fast, “We will be taking my car later.” The man didn’t budge. “Are you deaf or just stupid.. I said you can leave.” Oswald snarled, hand gripped firmly around the knife in his pocket. The driver merely smiled. “As you wish… Penguin.”

Oswald waited until the tail lights of the car could no longer be seen before he stormed into his home. He ascended the stairs with quickening steps, angry at himself, angry at you and above all angry at Galavan. Yet again his pride and arrogance had undermined him. He thought few people knew about you, but he should have known. Few people had known about his mother, and yet Galavan still had abducted her.

Perhaps Fish was smart about telling everyone her mother was dead. Oswald knew better, since after hours Fish had always let a little old lady sing on stage. People don’t go looking for the dead to get revenge on them.  
He slammed the heavy oak door open, hands shaking in fury when he saw you. You were just zipping up your dress, hair primped and makeup flawless. To think that you would go out looking like that with Theo Galavan…. it made his blood boil.

“You” He snarked, “are in so much trouble.” he locked the door behind him.

“Oh?” You raised an eyebrow at him, sliding in the diamond earrings he’d gifted you.

Oswald hobbled over and slammed his fist on the vanity table. The perfume bottles and pots of makeup shook and you jumped. He gripped your wrists, shooting daggers of loathing at you. “How dare you. Dressing like this. FOR GALAVAN.” Oswald tore at his scarf and forced it in your mouth, tying the ends around your head, a gag of sorts. He didn’t want to hear your excuses. Wrists were bound with his tie.

Ignoring your sputtering protests, he dragged you to the bed, fighting against you every inch of the way. “You’re min-ompf!” You’d gotten in a knee to his stomach, knocking some of the air out of him. This only made him more furious. “Mine.” He spat the words with hate, spittle flying across your face as you screamed muffled fury at him.

Oswald ripped at your dress, exposing his favourite set of lingerie on you. “Really? Did he tell you to dress like this? Or are you such a power hungry slut? I bet you were looking forward to crawling on all fours to suck his dick.” He ripped away the scraps of lace, leaving angry red marks.

“You’re even wet already at the thought.” He had swiped his gloved fingers at your center, pulling them away and rubbing the juices together between thumb and fingers. The soft kid leather stained and he smirked. “My flighty temptress, I will remind you of exactly who I am.” Oswald warned you as he crawled on top of you, holding your body down with his own. He relished how your eyes were lit up with anger and arousal, he could almost guarantee they mirrored his own.”I am your master.”

As he fumbled with his pants, you took that moment to twist and wiggle your wrists out of the silken tie. You pushed him over, straddling his waist and sinking down onto his hardened length. Pulling off the gag and throwing it aside, you hissed, “And I am a hurricane. Don’t you forget that.” Oswald glared, but let you have this. He grasped your hips urging you down and you moaned at the feeling of those leather gloves against your bare skin. The pace was fast as you rode him hard, screaming his name into your climax. Oswald rolled you underneath him and kept pounding away. “Filthy,” he accentuated each word with a snap of his hips, “Fucking.” he grasped his hands around your throat, “Whore.”

He pulled out to cum over your body, spurting the viscous fluid over your tits. “Bet Galavan wouldn’t fuck you like that.” Oswald panted, his anger ebbing away after he found his release, collapsing on the bed next to you.  
“I certainly hope not. “ You said, trying to regain your breath.

“What?” Oswald wasn’t sure he was hearing things right.

You made a funny snorting sound, “You actually think I would go to Theo Galavan’s? After all he has done to you?”

Oswald was flabbergasted, “But the driver… waiting at the door.”

“I told him to fuck off ages ago. I was actually hoping we could go out tonight. “ You paused, “But I think I preferred this. You should wear those gloves in the bedroom more often.”


	8. No More (Fight sex)

“I can’t do this anymore.” You suddenly announced in the middle of dinner. Oswald looked sharply up at you. You waved your hand across the room.

“What do you mean?” Oswald asked, a steely expression in his gaze.

“This! I can’t do this. You just had someone killed at dinner!” You gestured at the stained area of carpet where blood had pooled. Oswald had knifed a man in a fit of rage over delivering bad news just as you were sitting down for your meal.

Oswald very quietly said, “You’re not leaving.” He snapped his fingers “Close the doors. You will not open them to anyone but me, no matter what you hear.” he commanded. His hired men stepped out and shut the doors.   
Your eyes followed their movements, the click of the lock cementing your fate. Your blood boiled. How dare he!

“I hate you!” You screamed at him, releasing your pent up anger by hefting your wine glass at him. It missed and shattered against the wall leaving a red stain that dripped down to the floor.

Oswald’s expression had gone from neutral to outright fury in an instant. “I have given you everything!” He yelled back at you, his knuckles white as he gripped his fork. “You have no idea what I have done to get us here!”  
You froze, fury building within you. “I have no idea? FUCKING BULLSHIT COBBLEPOT. I have always known exactly what you did to get here. You may be the King of Gotham, but I remember when you were an umbrella boy.” You snarled, “I have been with you through all of this. Don’t think I’m a naive little fool.”

He stalked up to you and you continued to step back until you could feel the wall behind you. Still he advanced, shaking with anger.

“Oh but you are a little fool.” he hissed invading your personal space. “You don’t just get to say you’re leaving me… especially not after admitting you know everything I’ve done.”

“You think I’d rat you out?!”

“It’s hard to say. Apparently I don’t know you as well as I thought. Perhaps you’re even cheating on me. My mother always did say you were a hussy. Maybe you’ve spent your free time sucking off the men I assigned to you.”  
At Oswald’s harsh words you raised your hand and slapped him. He gingerly touched the now sensitive skin. Angered, he reached to grasp your hips and you smacked his hands away. Oswald’s lips curled into a sneer. He ignored your efforts to shove him off and fought against you to gather your wrists in his hands. You struggled against him, but in the end he succeed and dragged them over your head, pinning you to the wall as he ground into you.

“How fucking dare you!” You spat at him.

You had to admit to yourself that this side of Oswald excited you. How his hardness ground against your hip and his sharp aggressive bites along your collarbone made heat pool in your panties.

“Fuck you Cobblepot!” you cursed at him, attempting to tug your wrists out of his iron clad grip.

“Well if you insist…” Oswald spun you against the wall face first. He had your wrists in one hand. You could hear the soft sound of him unzipping his pants. He kicked your legs open and pushed the hem of your dress up.  
“Don’t you fucking dare.” You swore at him.

“Dare what?” He whispered in your ear. “To fuck my woman?” He pushed aside your panties to roughly feeling your wet and willing cunt. “You’re mine. I’ll have you anyway I fucking want.”

He positioned himself and thrust in roughly. You let out a cry of pleasure as he hit your g-spot over and over again. So close…you could feel yourself beginning to tighten and then. ..  
Oswald pulled out and dragged you around, forcing your pliant body to your knees.

“Suck it.”

You glared at him and opened your mouth to tell him exactly what he could do with his dripping hard dick. However Oswald took advantage of that and grasped his hands around your head, forcing his cock inside your moist warm mouth.

He cursed repeatedly as he fucked your mouth relentlessly. You gagged around him as he came, shooting spurts of cum down your throat. “Take it like the cheating cunt you are.” Oswald shuddered, closing his eyes in pleasure while his grip on you relaxed.

Wiping your mouth you stood up and slapped him again, this time raking nails across his face. “You’re a fucking selfish dick, Cobblepot.”

He ignored the crimson lines trailing on his cheek to glare at you. “Selfish?” he questioned, eyes narrowing in fury.

“Selfish.” you affirmed, “You always have me for your own pleasure. Never once have you been able to get me off properly.”

“Well perhaps you should be more like me and take what you want.” he taunted you, tucking himself away and zipping his pants.

Fine. You could play this game. “You’re going to put that silver tongue of yours to good use for once.”

You pushed him against the wall, relishing at his grunt of pain when his body contacted the hard plane. You grasped his lapels and kissed him harshly. He, in turn, yanked at your hair and shoved you back, advancing on you with a predatory gleam in his eyes.

“Fine. We’ll see how fucking selfish I am now.”

Oswald grasped your waist and hoisted you onto the table, bringing you down with a hard thunk. You shook your hair out of your face and he delved his hands under your skirt, tearing away your ruined panties. You applied pressure to his shoulders and forced him down on his knees. He swung one of your legs over his shoulder, biting and kissing along the inside of your leg. You could feel the warm brush of his blood as it smeared along your thigh when he ventured aggressively to your heat. He proceeded to lick and nibble at your most sensitive areas. You had already been so close and you could feel the tension building as he fingered you, quickly finding your g-spot to stimulate.

You threw your head back, hands buried in his hair, encouraging him. “Oswald, fucking- yes!” You cried out, tightening your thighs around him. He sucked on your clit in response, hands raking red lines across the outside of your thighs as you clenched around him. Your body relaxed as you came down from your orgasm, and Oswald shifted to get up. Winching as he put too much pressure on his bad leg.

He kissed you long and slow, forcing his tongue in so you could taste your own juices.

“Still leaving me?” he whispered against your lips.

“Not if we’re having sex like that,” you teased and winked at him. He smirked in response. “I’m very curious as to how many orgasms I can make you have in one evening. I’ll have to make up for being neglectful.”


	9. A Queen Protects (Clingy Sex)

You woke when Oswald pulled you to him, his kisses desperate against your skin. “Don’t leave me… don’t ever leave me. Promise me that.” He begged between each brush of skin.

“Darling, what’s wrong?” You asked sleepily, brushing your hand through his hair. Blinking away sleep, he came into view properly. Oswald’s expression was one of panic and frantic worry. He quivered in your arms, trying to articulate exactly what he meant. “I dreamt you left me. You betrayed and abandoned me.”

Your heart cried out for him. For his fears. Oswald was never truly confident in your love, in your affection. Drawing him to you, you kissed away his tears, slowly sliding off his pajamas. His ached for the feel of you, for every moan he knew he could garner from your lips. He wanted your love, your affection, your giving body. He melted into you, craving your gentle loving touch. Wrapping your legs around his slim hips, he thrust into you tenderly. He took his time as you whispered how much you love him with each kiss. Your hands rested on his shoulders, bracing him as he moved above you.

“You are mine Oswald, I will never relinquish you. I will never betray you, and above all I will never abandon you.” You panted, dewy sweat making your skin sheen in the pale moonlight. Rolling him over, you straddled him, sliding up and down, making soft moans at each brush against the sweet spot inside of you. His eyes trained themselves on you, drinking in your honesty and openness. You bared your soul to him in that moment. He breathed in sharply and took control, rolling you underneath him and drawing your knees up sharply so he could thrust harder against you. “You’re mine.” Oswald demanded with desperation laced in his raspy voice. “Forever.”

He came with a cry and collapsed against you. “A queen always protects her king.” You whispered to him, as he wrapped himself in your arms, head resting against your chest. He fell back to sleep listening to the beat of your heart. You gently stroked his back soothingly, listening to his quiet breaths as they lulled you into a peaceful slumber.


	10. Dirty Baths (masturbation)

**Summary for the Chapter:**

> Oswald Cobblepot got left alone in your apartment. (Kink Challenge - Masturbation)

Oswald snooped around the apartment upon waking, wondering if he would find anything of use to him. You had left this morning for work after letting him sleep off a hangover on your couch. He liked going through your things without permission, letting his hands pass over each of your belongings. He didn’t know if there would come a time he might need a little blackmail against you.

However your house was clean. Nothing incriminating or particularly interesting caught his eye. Though your dresser drawers proved somewhat exciting as he did pause to smell the lingerie most indecently. He wondered who you wore these sheer lace garments for. Everything smelled of mint, with something slightly more primal lingering on the undergarments. He shuddered with pleasure, eyes shut as he breathed in deep. and placed the items back before closing the drawers. Pausing,he decide to pocket a pair of dark purple lace panties from the laundry.

The bathroom was next. Figuring you wouldn’t mind, he soaked in the bath for a good hour, enjoying the steaming hot water on his aching body. He now connected your continuing scent of mint with the shampoos and body wash that that were kept on the side of the tub.

Relaxing, he slowly let his mind wander, imagining you in this very bath. His body sighed in pleasure, hands stroking down his chest to curl around his growing erection. The first image that came to his mind was from last night. How you looked on the dancefloor, body glistening with dewy sweat as you moved seductively to the beat of the music. He’d been jealous last night as he watched you grind against other men. Now he imagined how you’d feel wrapped around his cock, the way you would scream his name as you rode him. Oswald could perfectly picture your head thrown back as he thrust into you, body wet from the water. How he would lean forward and lick the droplets from your skin, suckle and bit at your pert nipples. His pace picked up as he began to fuck his fist with vigor. Water splashed haphazardly against the floor, wetting the tile and soaking part of the towel he had tossed down.

“Fuck.” He moaned, head tilted back against the porcelain of the tub and eyes closed in ecstasy at the smooth feel of his cock thrusting into his hand, his thumb swiping over the head.

A few more pumps of his wrist and he came undone with a groan and relaxed back into the water.


	11. Punishment (Spanking)

It was late at night and Oswald still hadn’t come to bed. You were feeling sexually frustrated. Every single intimate moment you’d had together as of late, had been interrupted and the whole week he had spent teasing you relentlessly. Sneaking hands along the inside of your thigh during dinner or worse yet, when he had slowly stroked your folds under the table, fingers teasing your entrance during a business meeting. You were desperate for release, your thighs clenched together in an attempt to either satisfy or quell your desires in public. Oswald had spent the entire afternoon whispering about all the dirty things he wanted to do to you, while the pair of you looked over reports in his meeting hall. He’d left you aroused and wanting to drag him off in private. Instead, he’d dismissed you after dinner. Oswald had another meeting with Jim Gordon.

Deciding that enough was enough, you stroked yourself outside your panties, feeling the silken fabric begin to soak with your juices. Tugging a pillow between your legs you humped it, grateful for the beginning build of friction. Your hand reached down, fingers dipping inside, teasing your clit.

You breathlessly panted, eyes closed re-imagining his exact words from this afternoon. How he would bend you over his knee and finger fuck you into oblivion. “Oswald!” you moaned out.

“Yes?”

Your eyes shot open and your body stilled. Oswald was leaning against the doorway, watching you with a dangerous smirk on his lips. Embarrassed you quickly pulled your hand out of your panties and tugged the pillow away, drawing your knees up to your chin defensively.

“I see you’re being a naughty girl. Couldn’t wait for me? What a wanton little slut you are.” He stepped into the bedroom, limp prominent as he stalked towards you, shedding his suit jacket before sitting on the edge of the bed. He knew how wet you would get just at his voice uttering those filthy words. You bit your lip when he reached to feel how soaked your panties were,“Very naughty I see. I think I’ll have to punish you for this.” Oswald’s face was stern, a shadow of a smile ghosting over his features.

“Yes please,” You breathed, remembering his earlier words.

He adjusted himself on the bed and patted his knee, “Come here,” he commanded, his eyes following your every move as you draped yourself over his knees.

A shudder of pleasure washed over you as he slipped your panties off to caress the curve of your bum. Then his hand brought down in a sharp smack, leaving a pink blush behind. You yelped at the sting of his hand, not quite expecting Oswald to pin you down and spank you.

“My poor little dove.” He cooed, caressing the warm skin of your cheeks. Your face flushed with excitement and a tinge of humiliation as he slid his fingers between your legs, testing how aroused you were. “Such a wanton minx you must be. So needy and wet. You were probably cumming from my words alone this afternoon.” He brought his hand down against your ass again. You moaned a bit at the sharp feeling. “Oh god yes. Again, please.” You whispered.  
Oswald smirked, “Count them, hussy.” he demanded, striking your skin over and over again. “Is that all you are? A painted whore? Should I fuck your pretty little demon’s purse?”

“Please!” Tears pricked at the corners of your eyes and soft moaning sobs broke out as you counted each time his hand made contact with your stinging bum. You could feel his erection digging in underneath you, and you desperately wanted him.

Finally he stopped and pulled you up.”:Get on all fours.” He demanded, his fingers making quick work of opening his pants and letting his erection spring out. You were quick to settle yourself on the bed, eager for his cock to fill you. He clasped your hips and thrust in. A gasp escaped you at the sensation of the fabric of his pants brushing your sensitive skin with every hard thrust he gave.

“Fucking slut. Do you want my cock buried deep in you? I’ll fuck your pussy so hard you won’t be able to sit.” Oswald’s profanity spurred your begging moans on. “Everyone will know what a hussy you are. Scream my name.” He swore at you. 

“Penguin, please! Fuck!” You could barely string a words together to make a coherent thought while he was ramming into you. The use of his moniker only encouraged his quick thrusts, and Oswald drew back a hand to slap your ass again. Your orgasm washed over you in ripples, your cunt tightening around his cock.

“Fuck!” He grunted, giving one last hard thrust to spill his seed before he collapsed against you. Breathing heavily he rolled off and gathered you into his arms, kiss along your face where there were still traces of salty tears from his earlier administrations.

“I love you so much.” He reminded you over and over again between each adoring kiss. Feeling sore, but infinitely satisfied you cuddled into him. “I love you too darling.”


	12. Going to Hell (Inappropriate Locations)

It was turning into an addiction. This craving animalistic need to wrap his hand around his cock and bring himself to completion at the most inappropriate of times and places.

It all started with Fish Mooney.

She had taken Nikolai into her private room at the club. He had followed secretly, hoping to garner some information with his ear at the door. Instead he listened to them having sex… really good sex based on what he could hear. Feeling himself grow hard and he glanced around nervously. There was no one in the hallway and he dared to button his pants and slid his cool clammy hand around his semi hard cock. He leaned his head against the door, desperate to fuel his imagination with their sounds of pleasure while he created his own bliss with each firm stroke. Oswald bit the wrist of his jacket to muffle the groan that slipped out as he spurted within his black trousers. He wiped off his cum covered hand with a handkerchief and quickly moved away. The feeling of naughtiness and the worry of being caught fueled his need to jerk off outside Fish’s door whenever she ‘entertained’.

Then there was his betrayal. He was injured and waiting for death to come to him. Butch had handcuffed him and tossed him in an unused section of warehouse while he went to deal with the Detectives. Oswald figured this might be his last chance. It was awkward at first, trying to jerk off in handcuffs. But he found a rhythm on thrusting into his closed hands. He finished and tucked himself away just before Don Falcone showed up. His heart was racing. How humiliating it would have been to be caught like that. His cock twitched in response.

Stabbing the young man in the truck had felt good. It was exhilarating letting his anger out like that. He had taken the clothes of both young men and the one he’d hoped to ransom was tied and taped, tossed into a corner of the dingy trailer. The fear in the man’s eyes was enticing and Oswald palmed himself through his wrecked trousers. His hard on came quickly and he jerked himself off in front of his hostage. “Too bad your not useful for much else since you’re such a scamp, even your own mother won’t pay for you.” He muttered huskily, spraying his cum all over the man’s fearful and tear stricken face.

Returning to Gotham was a blessing. However, Oswald’s craving hadn’t been sated. Having a morning jerk off in the shower no longer did it. He was getting aroused at the most inappropriate moments. The thrill of besting Maroni and stealing his money while at the same time getting promoted from dishboy to manager was one of those moments. He locked himself in the staff room to have a quick wank. Later he had to restrain himself from pulling it out when he gathered the money. Instead he rubbed up against the one of the inside doorways, warm stickiness spreading in his briefs as he found release from that alone.

He couldn’t even resist the urge in Liza’s empty apartment. It was too tempting. Especially with her scent all around him. It reminded him of the first time he’d jerked off at Fish Mooney’s. The scent of lilac spurned him on and he wrapped a pair of her silk panties around his cock to help speed up his motions. He came with an guttural groan. Oswald was feeling devious when he left the cum soaked panties in her drawer.

The thought of Fish still made his body ache. He purposely used his injured hand after she had stabbed him to deal with his hard on. The mix of pain and pleasure was intoxicating.

It seemed that fear, suspense and adrenaline did all sort of fantastic things to his body. The entire drive out to the cabin with Maroni had him on edge. While Maroni stepped out for firewood Oswald wondered if he would have time to fist his throbbing cock and get a gun. He had to wait though, the gun was more important. After his altercation with Maroni and the junkyard, he was too tired to bring himself to completion when he collapsed into sleep on the side of the road. It wasn’t until he was on a bus with a bunch of church singers that he was able to get off. One of the women had offered him a blanket and he snuggled under it, quickly gripping his erection with subtle strokes. His elevated breathing was covered up by the chorus of voices around him.

Oswald knew he was going to hell. Might as well make it worth the fall.


	13. Confessions (Church Sex)

It was late at night and Oswald was walking you home from dinner. A few bangs went off as you passed an alleyway. Instantly your hand was in Oswalds and the pair of you were hurrying along. It wasn’t till the night lit up that you realized it was firecracker’s whizzing through the air.

Oswald let out a shaky laugh to match your jittered giggles. Light hearted relief poured through you and suddenly there was a electric rush zinging along your spine. In that moment you want him, 

“In here!” You giggled, grabbing Oswald’s hand in both of yours and pushing through the broken gate of an old church. He followed you through the entrance of the building. It was beautiful inside, but eerie in a way. The place was empty, having almost a neglected feeling to it, except for the burning vigil of candles by the alter. Oswald was soon distracted by you pressing him into a wall, the lingering taste of wine on your tongue as it caressed his own. Suddenly Oswald was the one flipping you around and pressing your body against the wall. 

Oswald had his hands all over you, tugging your blouse from the waistband of your skirt and sliding his fingers underneath to caress the smooth stretch of skin he found. “Anything to confess my dove?” Oswald murmured against your skin, nibbling his way down your neck.

You let out a breathy moan, eyes drifting open and catching sight of the confessional booths…

“I think perhaps I ought to confess my voracious need to fuck you in a confessional booth while you wear priest robes…”

His hands stilled and he gazed at you, a mixture of surprise and lust on his face. Then he was dragging you towards the booth, pulling the priest’s door open. “Oh we are lucky…” Oswald muttered, seeing the abandoned robe folded on the seat. It was a cramped space for him to struggle out of his jacket and pull on the robes. Then Oswald was sitting, looking rather smugly at you through the grate. His devious smile drew pools of arousal between your legs and you desperately slipped your hands over his robes and whispered breathlessly, “Forgive me father… for I have sinned…”

Oswald played along, resting his hands over yours, “How many days since your last confession, my dear?”

“I’m afraid I can’t recall. But I have sinned many times since.” You knelt before him, and Oswald caressed your cheek, running a thumb across your bottom lip. He would never get tired of you kneeling before him like this, with that seductive gaze and begging pout. Already he was imagining those lips encircled around his girth, hollowing your cheeks as you sucked him hard. He quickly glanced through the wooden grating at the confessioners side, ensuring that no one was currently seated there. That’s when his eyes were drawn down to a curious hole between the partitions.

“Oh my…. someone has been a naughty priest.” Oswald breathed. You followed his gaze, now taking note of the glory hole. Judging by Oswald’s darkening eyes and how his tongue flicked over his lips, he wanted to try that very much.  
Brushing your lips over his briefly, you stepped back, leaving to take your seat in the confessor’s side and drawing the heavy velvet curtain closed. “Tell me of all your sins, my child.” Oswald encouraged, his hands already opening his trousers and pulling out his length, softly stroking it as he listened.

“Impure thoughts. The oldest of all sins. I want to have carnal relations with a man to whom I am not married.” You whispered, voice lowering, “I dream about doing all sorts of depraved acts upon him.” He could see the outline of your body through the grate, how the faint light showed off your hand tugging your skirt up.

Oswald swallowed, “What kind of depraved acts?” He continued sliding his fist along his cock. It was hard and heavy in his hand within moments.

Licking your lips, you replied, “I want to take his cock in my mouth, to bring him to pleasure like a common street whore. Until he can’t stand it. Then he’ll drag me up and turn me over, fucking me from behind and tugging my hair.” Fingers inched up your skin as you neared your heated center. Already your juices were soaking through the thin panties you wore. “I often touch myself at night thinking about it.”

“I understand, my dear. These urges are natural. Have you had much practice in this manner?” Oswald bit his lip, wanting so very much to shove his cock straight through that glory hole and into your warm mouth.

Putting on a charming stutter, “No, Father, I have not. Do you think I should practice?!”

Gravely Oswald nodded, “Yes. It would be my upmost pleasure to aid you in such a task.” Then Oswald was pressing his hardness through the hole. Instantly you dropped to your knees in the booth, tasting and licking. You could hear his groans, through he tried to mask them into the voluminous fabric of his sleeves. Teasing the tip of his eager cock with gentle caresses of your tongue, you delved your own fingers into your folds, coating them with your arousal. Then you took him as deep as you could, suctioning on and sliding your mouth back and forth along his cock.

He could see your head bobbing down on him through the grate, but it wasn’t enough. Oswald wanted to be between your thighs, pulling screams of pleasure from your body as he plowed into you. “Stop!” He commanded, pulling his dick back and then in a few short moments, the curtain was pulled back and Oswald was on you, bracing you on the seat as he fumbled with the robes. Your hands desperately pulling your skirt up, scrunching it around your hips as he spread your legs, and then he was inside you. The pace was harsh, animalistic in nature. A mild fear of getting caught by patrons of the church edging Oswald to finish faster. Your hands gripped the front of his robes harshly as Oswald pounded into you, his hips snapping into yours as he drew closer to completion. “Fuck.” He cursed, the profanity slipping from his lips as he spilled, his orgasm shooting through his body as you clenched around him.

“Whose there?!” A man’s voice echoed throughout the church.

Both Oswald and your heads shot up, staring at each other in giddy panic. There was a sudden rush of tugging your skirt back into place and Oswald pulling his robe’s together. Then the pair of your were hand in hand, running out of the church, past a bewildered and slightly angry looking priest.

Once outside and safely away, you leaned in and whispered in Oswald’s ear.

“I wasn’t done confessing, Father.”


	14. Royal (semi public sex)

The renowned Gotham City Opera House. Oswald had spent many evenings walking by, listening to the swell and fall of music at the back doors until some stage hand came out for a smoke and shooed him away. But now he was king…. and king’s could do what they wanted. Even criminal ones.

Welcome to the end of eras

Oswald cast smug looks at his fellow patrons as he lead you through Gotham’s renowned Opera house. You were perfection, perfectly cut dress flowing over your figure, and glittering jewels adorning each pulse point. Oswald had spared no expense this evening. Men and women moved out of your way as Oswald lead you up the stairs. Tonight not only would you be celebrating your anniversary together, but also the success of Oswald’s new reign.

“Oh Oswald, it’s perfect!” You were delighted. The room was luxurious and far different from anything you’d imagined. The chairs had been replaced with a plush chaise, and a bucket of ice chilled the champagne he’d ordered in advance, while wine was waiting to be poured. Oswald personally took great pleasure in the mix of gothic and ironwork that blended together in a harsh aesthetic. His favourite part perhaps was the fact the booth was carefully shielded from others. Oswald wasn’t oblivious, he knew he had enemies, and he knew Gotham’s elite would only find his presence a insult to theirs.

Done my time and served my sentence

The house lights dimmed and Oswald found them cast into shadow, something he rather appreciated as he let his slide over the curve of your hip as you sat beside him on the couch, sipping the rich red between equally red lips as you viewed the entertainment with interest. Oswald had other ideas though. The light played over your skin, appealingly highlighting it to Oswald’s interest. The sharp exotic musk of your perfume washed over him as he buried his head in the curve of your neck. You tilted it, allowing him greater access to the column of your throat and Oswald hummed in appreciation.

If it feels good, tastes good

Oswald let his other hand brush up the side of your dress and then it was cupping your breast, giving it a gentle squeeze that had you pressing your thighs together at the indecency of all this. The opera was barely through the first half and already Oswald had you damp, an aching want spreading through your nether regions. He brushed his lips over the sweet spot on your neck and he could feel the shudder run down your spine. “You look so very beautiful tonight, my dove.” Oswald murmured, moving to nibble lightly as your skin. This earned him a breathy sigh as you relaxed against his chest and Oswald smirked to himself.

I see what’s mine and take it

With the softest brushes of the pads of his fingers brushing down your bare arms, Oswald turned you inside out. Even the most beautiful auria in the world could not compare to how Oswald made you feel. Each heavenly sigh that slipped through your lips caused a resonance in Oswald own body. He forgot he was in public, he forgot that Gotham’s rich were only feet away from him in another room. Right now his world consisted of you, and the ardent sounds of the stage only enhanced it.

Sycophants on velvet sofas

You pressed him down onto the velvet chaise, it’s rich burgundy a sharp contrast to Oswald’s dark suit. “Jacket off.” You commanded, shifting to lie between his legs. The slit of your dress, tugged up, revealing the smooth expanse of skin and Oswald was quick to compile.

I am so much more than royal

He bit at his lips, taking particular interest as you ensured your black lace gloves were fully pulled up before you reached to open his pressed trousers. A low breath whistled through his teeth as you pulled his hardening length free of it’s confines. God’s he could stay here forever, just you looking up at him with mischief in your eyes and those decadent lace gloves encircled over his cock tossing it into full attention.

He sucked the droplets of wine that glistened and collected over your lips. The dewy sweet taste reminiscent of warm summer evenings and Oswald wanted to drown in them. The feel of your lace gloved hand ghosting lightly over the girth of his erection had him desperate for more. More of your lips, more of your hand, more of your skin. Just more. He wanted everything, for greedy he was, as all Kings end up being.

If it feels good, tastes good, it must be mine.

“More.” He whispered harshly, those pretty blue eyes begging you as you teased him. Then you slid down his body and Oswald rolled his eyes back feeling your warm mouth around the tip, sucking lightly. Then he buried his hands in your hair, urging you faster.

Welcome to my world of fun

Oswald jerked and then your pretty mouth was flooded with his cum. It dribbled down the side of your lips and Oswald’s breathing escalated, “Let me see.” He requested huskily.

Obediently you opened your mouth, letting the liquid pool and slide over your lips. Oswald gave a low groan as you licked your lips and then visibly swallowed. The opera was now long forgotten as he pushed you back, sliding the expensive fabric up your legs, letting it pool around your waist and diving beneath it, placing your legs over his shoulders as he kneeled before you.

“Naughty minx.” Oswald murmured, noting the lack of panties that greeted him. He kissed up the apex of your thighs, until he reached your already slick center. His nose buried in your curls and soon he was pleasuring you with his tongue, licking at the juices pooled, seeking out your sensitive bud. Your breathy sighs soon turned into sharp cries that you muffled by biting the knuckles of your hands.

Then you were grabbing his hair, gripping it and pressing him closer as you neared your peak. Oswald renewed his efforts and then you were pushed over, crashing around him with a stifled scream. Then he emerged from beneath your skirt, a devious grin as he wiped his mouth clean.

Welcome to the end of eras.

Little did he know, it would be one of his last evenings as King. For the day always comes, where all King’s fall.


	15. Fantasize (mirror)

Oswald stared at himself in the full length mirror of his apartment, admiring how the newly tailored suit fitted so well. He’d never had anything this nice when working for Fish. Admittedly, he had never had the funds to have a custom fitted suit before. While Fish was a generous employer, it didn’t cover extravagant expenses for umbrella boys.

Running his hand over the expensive fabric, he caressed it, for a moment losing himself into the imagining of a beautiful woman touching him instead of his own hand. She would stroke the lapels of his jacket, teasing his nipples through the fabric, run a finger over the jewel of his cross tie before sliding down the buttons of his waistcoat and further still to cup his cock through the italian cloth. Oswald let out a groan, closing his eyes as he replayed the fantasy of how her hands with stroke him softly, teasing his length into fullness before reaching to unbuckle his pants.

Swallowing the excess saliva that flooded his mouth, Oswald opened his cerulean blue eyes to rest on his reflection. His hand was already drawing his stiffening member out, giving it long slow strokes as he brought it to full attention.  
Oswald closed his eyes, intent on diving back into immersing himself into the fantasy. This faceless woman would lick her hand, coating it in saliva to provide smooth lubrication as she stroked him. Then she would get on her knees, giving Oswald the perfect view of her plentiful cleavage, before she would take him in her moist warm mouth.

“That’s it. Suck away my dear. Taste your king.” Oswald commanded softly, thinking of the soft curves and plump lips that would be locked around his hard on.

A groan escaped him as Oswald braced one hand against the mirror, the other held stationary as his hips thrust into his saliva lined fist. Fluttering his eyes open, Oswald’s dilated pupils centered on watching his heavy cock fucking into his own hand, the pace changing as he brought himself closer to completion, before backing off. His thumb spread the precum that beaded at the slit around the velvety head, providing even more slide as he adjusted and tugged away.

Mouth open, releasing little puffing groans of air as Oswald felt his balls tighten and then he released, splattering cum across the mirror. It shattered the pristine reflection of Oswald’s pinkened cheeks, and lust driven eyes.  
Then his gaze was drawn to the droplets of cum on his new trousers. “Shit!” He cursed, irritated at himself for his weakness. Now he’d have to clean his trousers.


	16. Silent Chaos (Fingering)

The weekly meeting was getting heated… and not in the good way. Arguments were spreading amongst the underbosses of the Penguin’s empire. Beside you, Oswald was staying silent. Merely observing the chaos with barely contained irritation, grinding his teeth together.

Equally as irritated as your boss with the squabbling, you raised your voice and screamed, “Quiet!”

A sudden hush spread over the table, and Oswald gave a sly smile. “Thank you, my dear.” He addressed you, before casting a foul glare over the rest of the table, “If the rest of you are done fighting like children, perhaps we can get to the issue at hand. Our recent loss in revenue.”

“We should consider human trafficking.” Your gaze immediately snapped to the man who had uttered those words and you were half out of your seat, filled with rage, before you felt Oswald’s hand on your thigh. Oswald gave you a meaningful look and slowly you settled back against the hard wood of the chair.

“Keep your pet on a leash, Penguin” Gregory laughed. You had never liked him. He left an oily taste in your mouth with every sickening word that passed through those too full lips. The pedo-stach and squinty eyes didn’t help either.  
Penguin cleared his throat, ignoring the leash comment, “She is my trusted right hand woman, Gregory. You would do well to remember that. We will not participate in human trafficking. It’s a vile sick trade.” His voice was cold, and judgmental. “Should I find that any of you have, be rest assured that you will no longer have a seat at this table. Or a seat anywhere for that matter.” He added darkly.

There was an uncomfortable shuffle as some were now looking anywhere but at the Penguin. He took notice and mentally ticked off who he needed to look into. Gregory’s face had soured and he slumped back in a state of perpetulant irritation.

As the meeting continued, you suddenly realized that Oswald had never removed his hand from your thigh. His thumb was slowly stroking back and forth in a soothing pattern along the bare skin, edging closer to the hem of your mini skirt. Your heart was thundering in your chest as you glanced sideways at him. Oswald’s attention appeared to be elsewhere, his face resting in his unoccupied hand as he listened carefully to suggestions to boost trade. The volume of the room heightened as each person rallied to have themselves heard over another.

Your breath hitched as he fingered the edge of your skirt, a careful pause as he waited for your reaction. Leg’s opened slowly, and you were suddenly very thankful for the poor illumination of the room as a blush crept to your face. His fingers teased up the remaining expanse of skin, dipping into the crevice between your legs to slide along the lace of your panties. Already your juices were pooling, dampening the fabric. A quirk of your boss’s thin lips signalled that Oswald was pleased with what he found. Your legs spread wider, allowing those clever fingers of his to move aside your panties and stroke into you, stretching and thrusting with his fingers.

A shuddering breath was wrangled from you, and the man to your right gave you an odd look before returning to the argument at hand. Biting your lip, you struggled to contain the little sighs of pleasure that threatened to spill out of your mouth as Oswald’s fingers worked on you. The knot in your belly tightened with each stroke and curl of those beautiful fingers, and you could feel the impending orgasm building. Your eyes closed in pleasure, and Oswald cast a quick amused look at your face. How no one else had realized what was happening under the table was beyond him. You were flushed, and a erotic look of suppressed pleasure was dancing it’s way across your features. Lips swollen and tinged red from biting, and your eyes closed with breathing escalated. He collected every detail, wanting to imprint it in his mind for later.

He stimulated your clit, bringing your pleasure crashing down on you as juices gushed over his fingers. “Ahhhh.” You gasped, eyes popping open as the table went silent. Everyone was now looking at you.

“This meeting is dismissed.” Oswald announced, pulling their curious gazes away. “Get out.” His hand slipped away from between your thighs, though he kept it under the table while everyone dispersed.

You remained, still coming down from your bliss and hesitant to move, knowing the moist spot you’d leave on the leather when you finally did get up. Your thighs squeezed together, the insides slick and painted with evidence of your pleasure.

As the last attendee left the room, it was just Oswald and yourself left. He’d even motioned his guards to stand outside. Your hesitant gaze moved to watch him as he carefully wiped off the glistening juices that covered his fingers on a monogrammed handkerchief. Oswald got up from his own seat and leaned in to whisper in your ear, “Next time, I’d like to hear you scream for me.”

A shudder of desire ran through you and Oswald smirked. You watched as he held up the handkerchief to his nose and breathed in deep. “You smell delicious.” A little moan passed through your lips at his words.

“Be a good girl and get rid of Gregory for me, and perhaps I’ll dine between your legs.” Oswald mused, running a hand through your hair and placing a chaste kiss against your temples, before he excused himself and left you alone in the room.


	17. Desire (Threesome w/ Edward)

There was a restless energy to her, Edward decided as he sat rigidly on the couch in his apartment, watching Oswald’s underling trail fingers over his personal items. “Why does he call you Lark? I know it’s not your real name.” Edward asked suddenly, motioning to her boss snoozing on his bed. Oswald was curled up in blankets, his eyes closed in peacefulness.

“It’s a nickname.” She explained, distracted by some of the paintings on the walls. “When I first met Oswald I had a showgirl kind of job.” Edward could imagine easily. He’d seen how Oswald laid possessive hands over her, the occasional hungry kisses he demanded when Edward let his attention linger too long on Lark’s body. Worse yet was the evening Edward had woken to the sounds of his bed banging against the wall. A harsh jealousy had risen in him then. Oswald had practically taken over Edward’s apartment, using his wit and charm to draw Edward in, use him as he pleased, only to then invite Lark to stay. His personal “bodyguard”. She was just as taunting in her fitted clothes, oozing with confidence as she constantly invaded Edward’s space.

“She was good at it too.” Came Oswald’s voice. Edward glanced over at his newly woken friend. There was a odd calculating look in his eyes as they shifted between Edward and Lark. “She’s good at a lot of things.” There was a suggestive tone to his voice that Edward immediately picked up on.

Darkness rose in Edward. Did Oswald mean what he thought? The urge to touch Lark’s skin, throw her down and have her in any way he wanted, welled inside of him. But she was first and foremost Oswald’s, though in many ways that bothered Edward as well. Though he had already had intimate relations with Oswald, he wanted Lark too. Oswald was dominating, preferring to top Edward and bring him to heel. He liked power, and Edward so desperately wanted a taste of it for himself. Judging by Oswald and Lark’s relationship, she would be willing to bend to his fancies.

He almost missed the sidelong glance that she gave to Oswald. However he did not miss Oswald’s subtle nod and the wicked smile that lit his face. So perhaps we can come out to play….Edward’s inner voice cooed eagerly. Lark was now slowly removing her fitted blazer, revealing a sheer blouse underneath. Her hands roamed across her body, squeezing along her breasts as she gave Edward a teasing show.

“Isn’t she beautiful?” Oswald murmured, moving from the bed to stand behind Edward. His hands rested along Edward’s shoulders as he leaned down to whisper into his ear. “Do you want her?”

Edward’s attention was entirely on Lark. How she moved, how she was slowly dropping away each layer of her clothes, revealing the charming expanse of skin that Edward had truly wanted to see ever since he’d walked in to Oswald’s panting moans as she sucked him off.. “Yes…” He replied to Oswald’s question.

The dark haired man smiled. This is how he would own Edward completely. “You can have her… if you let me take what I want.” Oswald suggested coyly, stroking his hand down Edward’s back and toying with the waistband of his trousers.

Edward was thrilled by this. Instantly he was on his feet, pulling Lark into his arms and kissing her. Then Oswald was pressing behind him, caressing the sides of his chest and drawing them down, sliding along his hips and thighs. He could feel Oswald’s erection pressing into the back of his leg. Soon he was distracted though. Lark had her hands in his pants already and was slowly stroking him as she sucked on his tongue. In an awkward dance of shedding clothes, Edward was crumbling to the floor, drawing Lark down with him as she finished rolling a condom over his cock with her mouth. Oswald followed, a bottle of lube in his hands. Slicking his own cock, he positioned himself behind Edward. His cock was hard and heavy in his hands as he stroked it, eyeing Edward’s arse with anticipation despite already having taken Edward the night previously when Lark was unavailable.

Already Edward was molding Lark to his liking, kissing across her naval, stroking her body with his long fingers. Then he was spreading her legs and coating the head of his cock in her juices before plunging in with a groan. It seemed like it had been so long since he’d felt such completeness. Her walls were tight around him and he almost forgot about Oswald as he pumped his hips into her. Then Oswald’s clever fingers were slick and pressing against Edward’s rear. He slowed his thrusts, softly bumping into Lark as they kissed throughout Oswald preparing him. The muscles had already been stretched, far more willing to comply then the last time.

Oswald’s breath was hot against Edward’s back as he lined his condom covered cock up with Edward’s entrance. Then he was pushing in slowly, Edward stilled completely to accommodate him. “That’s it, Eddie boy…” Oswald cooed, pressing feather light kisses along Edward’s shoulders. He felt full, struggling to maintain any sort of even pace as Oswald thrust into him and Edward, in turn, fucked Lark. She was moaning beneath him.”I want to hear you sing,”   
Edward demanded from her. Her pleasure ascending as he pressed a thumb along her clit, stimulating the small bundle of nerves till she was screaming his name as she clenched around him, milking his cock with her walls.

Edward’s tongue flicked out, sliding along his bottom lip as he drank in the sight of her quivering body. His own pleasure was becoming a hazy mix of lust and begging want. The head of Oswald’s cock was brushing against Edward’s g-spot, and already Edward was getting sloppy and desperate. “Please!” He cried out, his own release imminent as Oswald pounded into him. Then Edward was cumming, shuddering over Lark’s body, his arms barely holding him upright over her. Oswald was the last to find his pleasure as Edward’s own body clamped down on him. The tightness was intoxicating and Oswald bit into Edward’s shoulder. He continued to fuck Edward, his hand reach around to pull off the condom and slide along Edward’s slowly rising length. Oswald fully planned to bring him to the brink and leave him desperate. Then Oswald grunted, finding his own euphoric release.

They collapsed in a sweaty heap on the floor, arms and legs entangled as they each tried to regulate their breathing. Oswald was the first to get up, disposing of the condom and heading for the shower. Having his personal needs filled, he was content and relaxed. Edward and Lark however were still in a state of desire. Oswald had left Edward with a second, forced hard on. One that had Edward dragging Lark’s pussy over his girth as he tried draw another orgasm out of his strung out body. His nerves were frayed, and he desperately bucked his hips into her as she rode him roughly, rocking her hips to bring another wave of pleasure over her.

A dry orgasm ripped through him, and Edward groaned, relaxing underneath her. Lark moved her body up, positioning her dripping slit over his face. “Put that mouth to good use Riddles.” She demanded.

Edward complied, his hands supporting her hips as his tongue tasted and licked at her juices. Soon she was withering over him, crying out her pleasure as he sucked, drawing her orgasm out.

“I told you she was good.” Oswald stood in the doorway of the bathroom, a robe loosely thrown over his body and cinched around his waist. She got up languidly, kissing Oswald and then brushing past him, headed for the shower. Edward was left on the floor, trying to pull together a train of thought.


	18. Delicious Secrets (Sex language in public)

You were seated on the open patio at Oswald’s favourite new restaurant. He had invited Edward Nygma to join the table when he noticed the tall man walking down the sidewalk. Since he was busy discussing business with Edward, you had taken upon yourself to order lunch for the table.

“You know I prefer salmon over tuna.” Oswald commented taking a wandering glance as a beautiful young woman walked by him.You eyed her how her fitted dress showcased her curves perfectly, before responding, “Well then order your own food. I am certainly are not going out for dinner with you tonight if you keep acting like that. The clams at Bamonte probably wouldn’t even open to your prying touch.” Oswald grinned cheekily at your waspish tone.

Ed glanced between the two of you. Luncheon was turning into a complicated affair. He wasn’t sure what was going on, but his quick mind was starting to guess. “Well I like seafood.” he commented, attempting to fit into this unusual conversation. “I don’t like onions.”

Oswald ignored his comment and reached across the table to grasp your hand firmly in his own. “Pity the Greek place you so loved closed.” He reminded you, his voice underlined a threat.

You frowned at him. “Whose fault was that? Certainly not mine.” Well it might be yours. You had after all flirted with the owner knowing full well Oswald was watching. You enjoyed torturing him a little too much. Pity that he’s reacted by buying the restaurant and shutting it down, including blacklisting the owner from ever having a good reputation in Gotham ever again.

It was part of the game the pair of you played. Seeing who could infuriate the other more. It always lead to the most fantastic makeup sex. Absolutely mind blowing if you did say so yourself. Lately your game had turned into referencing every sexual act or misdemeanor by using food terms. By the time you left public company and found yourself in private, Oswald was always so unrestrained.

“We obviously remember it differently.” Oswald said, he squeezed your hand before retreating back into his seat. He picked an apple from the fruit basket placed in the center of your table, and drew his pocket knife to slice it apart. You winked at him, before turning your attention to Ed.

“Seafood, you say? What an appetite you must have. I understand it’s a bit of a aphrodisiac.” The suggestiveness in your voice turned Ed’s ears pink and he coughed discreetly. Your plump lips curved into a smirk and you caught Oswald’s furious eye.

“I think I’m ready for dessert.” You announced, waving down one of the waiters. She returned with the dessert menu, which you gladly took.

Deciding on something to tease Oswald with, you choose the cheesecake adorned with chocolate sauce and a order of generous whipcream and whole strawberries on the side. Oswald licked his lips when you announced your choice. He declined to order, knowing exactly what kind of dessert he would get to sample after lunch.

Ed declined dessert, and informed you that he must return to work. Oswald smiled and stood to shake his friend’s hand. “Thank you for joining us. We shall have to meet again soon.”

When he sat back down, your dessert had arrived. You teased Oswald with dipping the strawberries in the whipped cream and swirling your tongue over it to catch any errant juices. He swallowed, watching you intently as you finished your cheesecake and strawberries. He smiled slightly seeing a dash of whipcream remaining on the side of your lip. “You missed a spot.” He whispered to you. Leaning forward her kissed it away, tilting your head to gain better access to your lips.

You feigned a surprised look when he finally released you, “Did I? Oh dear. I’m so glad you noticed.”

Running your hand under the table you stroked teasingly along his leg. “Why don’t we go for icecream?” You asked suavely. You knew your hidden suggestion would be eagerly received.

Oswald snapped his fingers for the cheque. “I’d love to.” He was looking forward to your antics.


	19. Puzzle Piece (fluff)

Oswald sighed in happiness, burying his nose in the crook of your neck as he spooned around you. This was the sweetest of dreams. You here…in his arms. The world falling away around him until all that remained was you… you and your love.

He’d thought he’d never be able to find such a cherished person as yourself. But here you were. You’d fallen into his life, a spilled coffee over a cheap suit. Not one of his better days he assured you. But you’d insisted, blotting away at the stain, looking up at him with those attentive luminous eyes. He’d been transfixed. Words couldn’t describe you adequately. Not the way he wanted them to. It had been easy convincing you to dinner that night, and almost every time after that. Until you fitted into his life like a puzzle piece. Something simply meant to be.

Once he’d tried to explain his feelings, comparing you beauty to any number of things. But you’d smiled, blushed and glanced away abashed by his boldness. “I know” The finger placed upon his lips was gentle in stopping the flow of his words. But what truly did it, was when your lips replaced them. He’d found home again. And it was in your arms. There was no looking back from that. Oswald never wanted to. It had been months since he’d made you his, and still he woke in wonderment. Perhaps good things really did come to good people.

“I love you.” Oswald whispered, brushing a tendril of your hair away as he gazed down upon you. The early morning sunshine filtered through the gauzy curtains, lighting up your skin and warming it further to the touch. Rolling over in his arms, you faced him. Your smile content and eyes just blinking the sleep away. “As I love you.” Came your sweet reply.

Already you could feel him stirring, such evidence of his desire for you as he caressed one hand down your side, smoothing over your curves and dipping to the apex of your thighs. Oswald adored watching the small expressions of bliss contort over your face as he worked his fingers over your mound, parting the folds to find his treasure. The sweetest river would run for him, slick with your honey as he pleasured you. Each breathless cry from your lips was golden to him. “Oswald… please. Stop teasing.” You begged, your fingers drawing over his bare chest as you drew your leg up and over his hip. He matched your smile, rolling his hips up to tease your entrance with the head of his cock, smearing it in your juices.

Oswald bruised your mouth with his kiss as he pressed in, filling you to the hilt. It felt so divine, the fullness of him rocking inside of you. How sweet his love was, so gentle compared to the violence you knew his hands were capable of. Those dexterous fingers, memorizing each curve of your body, each brush of your skin sent shivers down your back. Rolling him onto his back, you followed, keeping him inside as you rode him.

His palms steadied you, guiding your heated core down onto him with each swirl of your hips. Leaning back, you balanced your hands on his thighs, presenting your breasts forward enticingly. Oswald shuddered, eyes fixated on how beautiful you looked. So carefree, so very freeing in this moment. He groaned, matching your soft cries of pleasure as he thrust up into you, meeting every bounce on his cock harder and harder.

Dropping one hand from your hip, he thumbed your clit, watching your eyes as they dilated and you bit your lip at the extra pleasure he provided. “Oswald..please… I..” He felt your walls contracting around him, beginning to milk him as your orgasm washed over you. Breaking upon you like waves over the rocks. Oswald supported your back with one hand as he took his chance to change positions, pressing you underneath him as he began pounding into your core. He was was so close, so ready to find his release in you. Nails raking up his back, Oswald shuddered at the generous mix of pain and pleasure before capturing your lips with his once more.

His hips snapped into yours, and Oswald gripped your thighs, pressing them against your chest as he pressed in deep. “Fuck…” Oswald swore, feeling his own impending orgasm hit and he thrust through it, spilling into you. His pace slowed, sloppy in his rhythm as he came down from his high.

“I love you, my dove.” Oswald soothed, whispering his affection to you. Those bright eyes of his bore into your own. There was only truth and adoration there. The way he pressed messy kisses to your cooling skin as you each tried to regain your breath. Oswald slipped out, the evidence of his love slick against your thighs and he cuddled into you once more. He was content. Happy. Blessed.

You were his love, his world. Heaven help whoever tried to take that away from him.


	20. Predator (Subwald ) Part 1/2

Oswald’s lips spread into a happy smile as he took into the finery before him at the dinner table. He had family again. His father was gracious and welcoming, insisting he stay with them. Grace, his stepmother, was more…. Frosty. His new brother and sister ere pleasant enough as well, but then there was Sacha’s friend who was currently staying with them.

He shot a brief jittering smile to his sister’s friend. You were elegant, assured of yourself and had been giving him predatory glances all evening. Oswald wasn’t sure what you meant by it, he was often surprised by how easily you invaded his space. A touch here and there, you insisting upon him leading you into dinner. The meal was well underway, the clink of cutlery against fine china as the family ate. Conversation was light, brushing over each topic like butterfly wings.

Oswald jerked suddenly, the feel of a feminine hand sliding along his thigh. Nervously he gulped his wine, and shot a glance over to you beside him. You smiled at him coyly, hand moving closer until you reached his crotch and squeezed. He sputtered, and Elijah looked at him in alarm. “Oswald, my boy, are you quite alright?”

You were quick to answer, covering Oswald’s shock, “He’s fine. Something perhaps just went down the wrong way.”

The warning look you gave him silenced the words about to leave his lips. “Yes, father. Just… went down the wrong way.” His lashes fluttered, eyes watery as he hid his distress.

Your hand began to stroke him, and Oswald bit back a whimper as his body betrayed him. It felt… good. He could remember this, how good it felt when someone else’s hand was on… well.. Oswald didn’t want to think about it. He recalled Hugo’s aversion therapy well.

It was so wrong, you were his sister’s friend. Worse yet, one he’d just met. He shouldn’t feel like this. Oswald hated that his breath hitched and all he wanted was to feel your soft hands over his length. He shifted, finding a more comfortable position in his chair. Sweat was collecting along his neck, dampening the collar of his shirt as you teased him, his length hard and pressing against the expensive fabric of his suit.

Elijah gave Oswald another concerned look, but he was hesitant in pressing the matter. In fact, Elijah was hesitate in pressing a lot of matters, especially concerning his family. He tried to ignore the flickering expressions that crossed his son’s face.

You continued to rub along his clothed cock, thumb expertly finding the head and Oswald jerked, biting his lip as he closed his eyes. It was too easy to give himself over to the feelings of pent up frustration and cave to your pleasurable touch.

Oswald muffled a groan of satisfaction as his orgasm hit, his cock twitching and spurting inside his trousers. He looked up from his wine glass to see the rest of his family staring at him curiously. “This wine… it’s quite good.” He covered up feabily, now mortified that he’d just cum in front of his new kin. A familiar heat spread across his cheeks, and Oswald hoped they would put it down to the wine. He was filled with disgust and humiliation at himself for being so easily perverted.

You smirked, withdrawing your hand, “Indeed, simply the finest. Almost… orgasmic, would you say?” You toyed with him like a cat with a mouse. He gulped, and a nervous laugh escaped, “Indeed….”

His fingers were quivering and Oswald lost hold of his wine, the glass tipping and spilling over his lap. “God heavens, I’m so sorry. I … excuse me.” He set the glass down and patted at his clothes with a cloth napkin, before rushing out of the dining room.

Elijah rose to follow him, but you put up a hand. “I’ll make sure he’s okay.”

Smoothly you exited, Oswald’s unique gait easy to following in the silence of the old house. He’d gone to the bathroom, and you pushed in behind him. “I… please don’t. I shouldn’t have let you…” Oswald stammered, looking up at you in hesitation.

Rolling your eyes, you locked the door after yourself and cornered Oswald. “Shut up, will you?

He was so easily subjective to you,and you fed off it, stroking along his jacket and brushing feather light kisses along his jaw as he froze. “Please…I… we shouldn’t.” He whispered, staring at you in surprise as you took his hand and guided it under your skirt. His fingers trembled against your skin. The lack of panties allowed him to easily press his fingers in, letting him feel how wet you were. It took some encouragement, but soon you had Oswald fingering you without guidance. His expression changed from one of panicked shock to one of fascination as he watched your face.

It was flushed, your lips plump and pinkened from biting them as he pumped his fingers in and out. “That’s it… “ You cooed, hands gripping and sliding over his clothes as you let yourself balance against him, feeling your body tingling and building towards the rush you had so craved since meeting him. There was a franticness about you as you trembled, and cut back a small cry of release from your lips. Oswald’s fingers paused, feeling your walls tighten around him then gushing, juices running over his fingers.

“Suck them.” You demanded, breathlessly coming down from your high. Tentatively Oswald place his fingers against his mouth, tongue flicking out and tasting you. “Suck them clean.” You insisted, sharp eyes watching him.  
Oswald complied, the taste tangy in his mouth. You rewarded him with a smile, “Good boy. This will be our little secret… now why don’t we take you upstairs to change… “ Your eyes were now on the obvious bulge in his pants and Oswald sucked in a sharp breath in trepidation of what was to come.


	21. Prey (Subswald) 2/2

Dinner was forgotten as you lead Oswald upstairs to his room. He was pliant under your touch as you pressed him hard against the door the moment it closed. You had no idea how easy it would be to subject him to your every whim.  
His hands were tentative against your body, as you kissed him. Oswald melted under you, your touch like fire to his skin as you tugged his bowtie free and starting making quick work of the buttons. Dishevelment looked good on him, those raven locks ruffled and messy, his eyes darkened with lust and thin lips reddened. You wanted him, his innocent manner so meek that you couldn’t wait to have him begging for your touch.

“I haven’t… it’s been a while…” He looked nervous as you rolled his suit jacket and shirt off. There was something weak and vulnerable about him, the paleness of his soft skin, the light dusting of hair over his chest that followed down to a darker patch near the waistline of his trousers. That was where the real prize was. You’d been imagining this moment for the past week.

He’d peaked your interest as soon as you arrived. Sacha had explained everything in her snotty lofty tone. Oswald was her stepfather’s son, newly reunited with the family. A crimelord until Arkham had set it’s claw into him, turning him into putty. The man before you was subservient, easily swayed and the hunter in you wanted him like a trophy. To have a man like Oswald Cobblepot quivering and begging before you… it was intoxicating just thinking about it.  
“Undress me.” You commanded softly, stepping back from him, calculating his every move. Oswald looked uncertain as to where to start and you flicked your fingers, gesturing to the zip on your dress. His fingers were tentative as he slowly pulled, the dress opening along your back. You could feel the gentle warmth of his breath against your spine and you shimmied your hips, letting the fabric fall in a soft pile around your ankles.

Turning your head slightly, you watched Oswald’s reaction. He was breathing quickly, his eyes trailing down the curve of your back, ghosting over the dark garter belt that was holding up sheer black stockings and following down the seams to the shine of your heels. “You’re exquisite.” He breathed, taking in the front view when you turned to face him. His hands were already moving of their own accord and you allowed him to cup your breasts, thumbs drifting over dusky nipples.

It was delightful how easy it was to draw sounds out of Oswald. Your hands were on his trousers, popping them open and pushing the ruined pants off his hips followed by his stiff underwear. Oswald helped shuffled his shoes off and awkwardly bent to peel off his socks as you retired to the bed, lounging against the soft sheets while you watched him.

Oswald flushed under your gaze and moved to cover himself, embarrassed of his own body and it’s obvious reactions.

Holding up a finger you shook your head, “Don’t. I want to see you. Bring your tie to me.” Oswald bit his lip, desire running through his body simply at the commanding tone of your voice. It felt good submitting to you, letting you lead him through this dance. The black length of fabric was clenched in his hand and he opened it, letting it unfurl and drop into your open palm. “Good.” Your praise filled him with warmth and Oswald crawled onto the bed, eager to see what you would ask of him next.

He let out a moan as the tips of your fingers teased up his shaft and you smirked. “Lie back Oswald. Let me take control.” You soothed, pressing him against the pillows. Carefully you straddled him, his cock brushing against your stomach and twitching upon contact. So eager…

“We can’t have anyone hear us, so I’d like to gag you. Is that alright?” You asked, holding the tie up to him. He nodded, eyes trusting as you ran the fabric through his mouth and tightened it around his head. So pretty, you thought, stroking along his face. “You aren’t allowed to touch me until I say you can. If something makes you uncomfortable, the gag is easy to remove, just pull. Do you understand.”

Again he nodded, resting his hands against the covers and watching as you slinked down his body, coming to a rest between his legs. It was too wonderful not to tease him, featherlight touches along his weeping cock, denying him any kind of proper friction. Oswald was soon whimpering and squirming, his cock twitching as he clenched his fists, gathering the fabric underneath as he watched you. His pleads were muffled, head thrown back against the pillows as you finally let your lips encircle around the velvety head. His hips thrust up, desperate to fill your mouth and you pulled away with a popping sound.

“Tsk tsk. That wasn’t nice.”

Oswald whined, saliva soaking the fabric and collecting along the corners of his mouth as he watched you frantically. Again you teased him, licking along the sensitive underside until you decided he was ready to burst. Licking your lips seductively, you straddled him again, lining his throbbing cock up with your sopping cunt and sliding over him. He filled you completely, and you smirked watching Oswald’s eyes roll back and close.

You took your time riding him, hips rolling slowly in lazy circles and Oswald’s hands were drifting between the sheets and wanting to touch your hips. Finally you took pity upon him, “You may touch me now.” Instantly your words had effect, Oswald’s hands were gripping your hips hard as he hurried to pace, drawing you down onto him over and over again. He held you to him, rutting into you until he found his release and you muffled your groan of pleasure into his shoulder.

A gentle knock was against the door and you threw your head up quickly, hands scrambling to undo Oswald’s makeshift gag as Elijah’s voice drifted through the wood. “Oswald? Are you quite alright?”

Oswald was swallowing the excess saliva and you quickly dropped over the side of the bed as the door opened. “Oswald?” Elijah’s concerned face peered around the door just as Oswald hastily tugged a sheet over his lower half.  
“Fine… I’m fine. Just feeling a bit tired.” He lied surprisingly easily, and Elijah frowned but nodded. “I’m going to go sleep I think.” Oswald bobbed his head as he spoke, hoping his father wouldn’t come into the room and see the clothes strewn everywhere.

Instead his father gave him a brief smile, “Of course. Rest well my boy. I’ll check on you in the morning.”

The pounding of his heart echoed in Oswald’s ears as he waited with baited breath for the last sounds of his father’s footsteps down the hallway. You were already slipping your dress back on, and Oswald wondered out loud, “Will you stay?” He wanted you to, to cuddle next to you, breathing in the exotic perfume of your skin.

Frowning, you shook your head a twisted smile coming to your lips. “No. I got what I wanted.”

His heart fell, worry gnawing at it as you slipped out of his room. Whatever did you mean?


	22. Unwelcome Guest (threesome w/ Edward)

It was awkward in a way, sleeping like this. Oswald was becoming an unwelcome guest in Edward’s loft apartment. He refused to take the sofa, insisting it was too hard on his back and Edward, so eager to please his idol, allowed him the bed. Which left you feeling irate at sharing with two men, worse yet, sandwiched between them.

Edward tried to appease you, lying on his side, wrapping his lanky arms around you and holding you to him. It was still frustrating, with Oswald a permanent fixture, you couldn’t get any kind of private time with Edward.

Tonight was especially warm, you wore only a oversized t-shirt to bed and a long sigh escaped as you stared at the back of Oswald head. His hair was spiked and ruffled, but his chest rose with a steady rise and fall. Edward’s firm chest was behind you and his fingers slid over your hip, ruching the shirt up and toying with the waistband of your panties.

“Eddie!” You hissed, trying to keep quiet.

The low rumble of his laugh reverberated across your back. “He sleeps like the dead.” There was a pause as he shifted and you felt his teeth graze over your shoulder. “Come on… I’ve missed you. We’ll make a game of it… first to wake him loses.”

It was hard to resist, not when Edward’s fingers slid between your folds, teasing your clit and slicking themselves in your arousal. You bit back a moan, your teeth catching your bottom lip with eyes closed in pleasure as he slowly fingered you. Hips rolled back, brushing against his growing hard on and grinding back.

“Minx.” Edward whispered, pressing back and continuing his onslaught of your skin. It was terribly naughty, knowing Oswald was right next to you and unaware of what was happening.

He removed his hand from your panties to ease them down your hips, shoving them deeper under the covers as he adjusted to line up with your slick cunt. His cock was painfully hard, and he sighed as he guided it into your welcoming tight heat. Edward’s movements were slow, miniscule thrusts as he rocked into you and you sighed closing your eyes to the feeling of finally having him filling you.

Lost in the moment, you opened your eyes in surprise as a hand clasped your own. It wasn’t Edward’s long fingers over your own. These were shorter, more calloused.

They were Oswald’s. He brought your hand around over his hip, and placed it over his clothed bulge. “Go on.” Edward murmured, kissing and sucking at the sensitive spot under your ear and you ran your tongue across your teeth before sneaking your hand into Oswald’s pajama pants. His skin was hot, his cock throbbing and you experimentally swiped your thumb over the tip, spreading precum to help provide some lubrication.

The raven haired man’s breathed hitched as you stroked him, firm grip around his cock, matching each thrust of Edward;s with a firm toss of your wrist. “I want to see you,” He breathed, momentarily breaking the rhythm to turn and face you as he starting shrugging out of his pajamas.

Now there was no need for pretending now. Edward adjusted you, sitting up and sliding you back onto his cock as he slowly rocked into you, letting you lean your back against his chest while he watched Oswald’s expressions over your shoulder with interest.

“May I?” Oswald asked curiously, motioning towards your shirt. You nodded, and he slipped it up over your head and tossed it. Immediately his eyes were drawn to your breasts, and he bent his head to flick his tongue over a pert eager nipple. Fisting your hands through his hair you leaned back, turning your head to catch Edward in a kiss.

Oswald kissed and nibbled his way up your neck, finally capturing your lips for his own. It was hard to concentrate, with Edward gripping your hips and dragging you back onto him over and over, and Oswald’s fervent mouth upon your own, his hands caressing your breasts with the softest of touches. It was a overload of the senses.

“Fuck… darling I’m going to,..” Edward didn’t finish his sentence, instead dropping his head to your shoulder and giving a hard thrust as he spilled into you with a grunt. You whined at the loss of his contact as he slipped out, flopping back against the bed. His inquisitive brown eyes watched approvingly as Oswald distracted you, his thumb rubbing your clit and eliciting a begging cry from your lips.

Desperate for release you pressed Oswald back against the bed, straddling his thin hips and sliding your slick cunt over his cock. He closed his eyes, a blissful expression over his face as you swirled your hips and slammed down on him, hands balanced on his chest. Riding him hard, you could feel the pressure building, a tidal wave ready to break over your body. Slipping one hand down, you rubbed at yourself, finally enough friction to bring about a electrifying orgasm that had your walls clenching hard around Oswald’s cock and you crying out.

Oswald wasted no time, flipping you underneath him and pistoning his hips into you. Edward’s ready smirk filled your vision as you turned towards him. His hand was lazily stroking over his cock as he watched and he carefully leaned down to kiss you, his tongue sliding into your mouth and drawing out each delicious moan.

The wet sounds of your slopping sex filled the air and Oswald concentrated on his own release, each hard thrust of his hips bringing him closer. Finally on the brink, he pulled out, his hand clasping over his cock. It was slick with evidence of both Edward’s and your own orgasms, and he tossed it in his fist, eyes on the apex of your thighs that were dripping with juices. Suddenly he tensed, eyes squeezing shut and his mouth open in a wordless cry as his cock twitched and cum sprayed over your belly in thick ropes.

“Now you’ve made a mess, Mr. Penguin” Edward commented teasingly, breaking off his kisses to glance down at the shimmer of cum over the curve of your belly. He followed it down, long tongue sliding over it and licking it up. Oswald watched in fascination, even more unbelieving as Edward curved a palm around his neck and drew him into a long open mouthed kiss. He could taste himself on Edward’s tongue, briney and tangy.

You studied them with half lidded eyes, delicate hands reaching down between your splayed legs to toy with yourself. It was certainly erotic watching them kiss, Edward’s hand cupping Oswald’s face and the desperation with which the smaller man kissed.

“She’s so insatiable, isn’t she?” Edward commented, glancing at you sideways. Oswald watched you, his eyes dark with lust and his cock once again twitching with interest. “Whatever shall we do?” He asked his companion graciously. Edward smirked, “Are you hungry?”

Based on the curving smile, Oswald certainly was. Perhaps he wasn’t such an unwelcome guest after all.


	23. American Beauty (betrayal)

She’s an American beauty

Oswald could remember the first time he saw you. You were like fire to him. Gloriously beautiful in your radiance, but dangerous to touch. The strangeness of it all was that you had a keen interest in him from the moment you saw him. You’d pushed aside attentive handsome men, eyes on your prize as you strode from the bar right up to him, running your fingers up his arm, and introducing yourself with confidence.

I’m an American psycho

There seemed to be nothing about him that you didn’t like and Oswald took great personal pleasure in introducing you to his world. The last time he’d ever been so enamoured with a woman was Fish Mooney. You exuded the same power, the same sensuality. The way your lips formed his name…

I think I fell in love again

Everything about you was addicting. Oswald had never had anyone show him the attention nor devotion you bestowed before. You fawned over him, complimenting his every whim and he caved to it. It was reminiscent of his mother’s affection. How clever, how handsome, how brilliant he was. Oswald drank it in like a sweet nectar, your words dewy honey to his ears.

I’m the best worst thing that hasn’t happened to you yet

The first time you’d kissed him, Oswald suddenly understood why poems were written about love. How people could lose their minds over these feelings. They ruled his body, his mind, his soul. Oswald’s world now revolved around you. All he ever wanted was to feel you.

We’re the things that love destroyed

You pressed him against the wall, nails clawing over his suit and Oswald groaned into your mouth. “I need you.”

A growl of frustration slipped through your lips as you grew irate with how many layers he wore. The suit jacket was tossed to the floor quickly and your fingers worked at the buttons of his waistcoat. Oswald helped shrug it off, before he was distracted once again by your demanding kisses. Fingers slipped under his braces, snapping them off his shoulders and rushed hands pulled at his starched white shirt.

“You wear too many clothes.” You complained, breaking away and drawing in a quick breath.

Oswald was inclined to agree at this point. “I’ll get the rest.” He worked at the familiar buttons of his dress shirt as you took to undressing yourself. Slightly disappointed that he wouldn’t be the one to help you, he was pleasantly surprised by what you revealed.

The deep purple lace lingerie set revealed more than it covered with strategically placed straps, and Oswald suddenly felt like his trousers were too small. In his hurry to shed them, you sauntered over to the bed, sliding across it on your stomach. Looking up at Oswald with sultry eyes and a coy smile, you gently flicked your feet back and forth tauntingly, “Well Mr. Penguin, I would love to know what you do to bad girls like me?”

Your body was a temple he was going to desecrate. And desecrate it he did.

That night he whispered, “I love you.”

There was a uncertain pause, a fleeting tinge of panic to your eyes before it was masked. Instead of replying, you kissed him, dragging him back down to the bed and making him forget that you hadn’t returned his words of affection.  
we were only there, to make you live again

As sweet as you were on the surface, there was a tigress lurking beneath your skin. One who clawed and bit and screamed in ecstasy with each thrust of his hips. He had no idea that anyone could find pleasure from pain. You showed him, and every cry drawn from your body at his rough touch sent him into waves of pleasure. The way you begged for his hand harsh against your skin, or the moan of pleasure as his teeth sank in. He always marvelled at how you relished the marks he left, flaunting them about the bedroom and sometimes even beyond when he couldn’t resist something a little more visible. The shades of dusk marbled on your skin, with a scarf drawn down just enough to give a hint of it.

Us, we were pity sex, nothing more and nothing less

When he found out that you were merely stringing him along, Oswald was furious. The man who brought the news was beaten half to death, an act he mildly regretted. You weren’t to know. Not when he had other plans with how to deal with your…. Betrayal.

There was one last night together, one last chance. He pretended not to notice the marks that didn’t belong to him. The hand prints that were slightly too large against your skin. Afterwards, he watched you sleep, gently tracing the curve of your cheek, before placing a fated kiss to your forehead and leaving. 

Oswald stared pensively at the small music box sitting on his desk. You had gifted it to him. A reminder of yourself you said. Anger was being held back, the urge to break the box into thousands of pieces grasped his limbs. Instead his trembling fingers pushed it open, winding it back and letting the dancer twirl…

She’s an American beauty

Like all fires, you eventually had to burn out, Oswald mused listening to the slow tinkle of music. A simple knock against the open door and Oswald looked up to see Zsasz waiting.

“She’s dead as ordered, sir.”

“Thank you, Victor.” The crimelord waved his hitman off and gently closed the music box. It was a firm reminder, he was better off unencumbered. Oswald threw the box into the fire, shadows crossing his face as he watched it burn.

I’m an American psycho


	24. Metamorphosis (sex goes wrong/bondage)

Little Penguinella. All covered in dirt.” You teased cruelly, staring down at Oswald Cobblepot. He was on his hands and knees scrubbing at the floor, a bucket of soapy water beside him.

“Miss.” He looked up at you, eyes catching your patten leather heels first and then trailing up your sheer stockings, to the fitted skirt and blouse before finally resting on your smug expression.  
“I love a dirty man.” You stated, “You certainly look dirty.”

It was true. Despite the apron he wore, and the sleeve covers, Oswald had smudges of dirt across his face, and clothes. His stepmother had him weed the garden earlier and denied him any time to freshen his appearance.  
He was trying to apologise for his appearance, cheeks tinged pink in embarrassment as he explained. But you weren’t listening, you liked how he looked on his knees, all vulnerable and stuttering. Casually your foot struck out, hitting the bucket and tipping it over. Oswald’s pants were soaked, the water spreading over the floor

“Opps.” You pouted innocently as he gasped at the warm water. Oswald rushed to mop up the water, leaving the floor shiny and slippery.

“Peguinella…. You missed a spot.” Your firm voice left no room for complaint and Oswald looked around in confusion. The sharp tap of your heels against the floor drew his gaze down. There were splashes of water evident on them and he returned your look with one of uncertainty. “Well? Get down there and clean them.”

The sound of someone coming down the hall made you glance behind him, a wide smile spreading over your face, “Mrs. Van Dahl, I was just about to look for you. Are you sure it’s alright that I stay for the week? I hate to intrude on such a time. Mourning the loss of one’s husband, I simply can’t imagine.”

Grace returned your smile, “My dear, it’s always lovely to have you. It’s not an inconvenience at all. It would do to have some good cheer around here. Perhaps a little party… the staff is so dull.” She glanced at Oswald in disgust, something you took sharp note of.

“Oswald… why isn’t the floor done? Really… you look a disaster. Finish it and get cleaned up, I can’t have you serving dinner like that.” Grace wrinkled her nose at him, as though offended by his very presence. “I’ll go get Sacha, we’ll go out for a girls day. How does that sound?”

“Lovely.”

You watched Grace saunter off and turned back to Oswald, “You know… once upon a time, you wouldn’t hesitate to beat someone to death for what I just did. “

“I’m a changed man. I couldn’t.. I won’t hurt anyone.” He stammered earnestly.

Releasing a deep sigh you stepped forward, plucking at the apron. “If you change your mind, you know where to find me… Penguinella put my bags away. Be sure to unpack them for me so they’re ready when I return.”

Grace and her two children knew nothing of your past relations with the crime lord. You’d had a few evenings of passion with him here and there, and he had always been commanding and cruel to you. It felt rather strange prodded at him. You had been waiting for him to lash back, drag you off and teach you a lesson. Instead you got apologies. It actually surprised you that he had considered dropping to his feet to lick at your shoes. The Oswald of old would have insisted you be spanked for such impertinence. He had even accepted the name calling, another misdemeanor that would have you scrambling to make amends for.

It was an interesting coincidence that you’d encountered Mrs. Van Dahl at the funeral by chance. Your family was buried in the same cemetery, and you had once gone to school with both of her children. She of course, thought your family was marvelous. Old money as she had once commented. Old, dirty mob money, you had thought. Crime was in your blood, and she was oblivious to it. The only reason you had accepted her offer of a extended visit was when you’d overheard her conversation to Oswald.

It was curiosity that had you here. Would he really bend to that woman’s wishes? Apparently so. Grace returned, purse in hand, “Oswald, I want this all finished before dinner, along with your other chores. I also need you to polish the silverware.” She held her hand up to his protests, “You said you’d do anything to stay here Oswald… You have a roof over your head, food and family. Why are you arguing with me?”

Oswald fell silent, embarrassed and visibly upset as he tried to control his features, “I.. of course. You’re so sweet and kind Grace. Thank you.”

It was disgusting to watch, how he grovelled to her. You had to school your face into one of neutral disinterest before Grace turned her attention to you. “Oswald, It’s Mrs. Van Dahl.” She reminded him sternly, and linked arms with you, “Shall we go?”

Sacha was already waiting by the car, a bored expression on her face. “Oswald is simply a menace. His father insisted he stay. Too bad he didn’t drink the poison too.”

Grace shot her daugher a warning look, before soothing a smile your way, “Alcohol. His father mixed alcohol with his meds.. A terrible combination. Oswald is fortunate he hasn’t gained Elijah’s heart condition yet.”

You raised an eyebrow, deciding to play into her hands, creating a falsehood, “That’s too bad. I love a good murder story. How do you think I inherited so young?”

Sacha laughed, “See mother, I told you she was a dear.”

The atmosphere instantly relaxed, murderers suddenly at ease with the thought of other misdoings. As you shopped with them that afternoon, Sacha kept confiding in you, as though entirely pleased that her stepfather had died. She acted like it was her idea, that she ought to get a bigger share, even questioning your methods as to how your parents had died.

It was an easy fib, if only partially true. Your parents had died from poison, but it hadn’t been at your hands. The foxglove that had killed them was untraceable, unlike the drain cleaner that they had used. You found her technique sloppy, and her flippant attitude repulsive. A immature and dim girl who catered to her more manipulative mother. Oswald didn’t know. Not yet.

X.x

“Oswald, you haven’t unpacked my bags yet.” You snapped at him after a brief glance into your room.

He hobbled down the hallway, apologising in his high stammering voice. Everything about him was strained. You let him go into your room, taking a quick glance up and down for anyone else before following him. The door firmly shut behind you and you studied him for a moment as he went to open your bags.

It was too tempting to let him continue, so you held your tongue and simply watched him. He opened each of them, tinging pink when he got to your delicates. The lacey garments were familiar to him and he glanced at you, recalling the things he’d done. His eyes widened in surprise at the rope and crop hidden underneath all the silkenware. Arousal spurred in his body, and he tried to ignore it. He wasn’t that man anymore. The things you liked, he couldn’t deliver upon.

He placed each item of clothing away with quickness and turned to you, his eyes large and uncertain. “Is this adequate Mistress?”

“Stop calling me that Oswald. I’m not your Mistress.” You snapped, suddenly tired and you pressed your palms to your eyes heavily. It weighed on you. The knowledge that the people downstairs had tried to kill him, and instead took away the only family he had left. Family was everything to Oswald. Worse, they insulted him by making him a menial servant. Oswald Cobblepot had done far too much in his life to be brought down this low.

“But what if I want you to be?” He asked quietly, still watching you. Sliding your palms away, you frowned at him, “What?”

“Be my Mistress. Tell me what to do. Degrade me even.” Oswald looked uncertain of his words, afraid of what you would think.

Shaking your head, you stepped up to him, “Oswald you don’t want that. In all the time I’ve known you… you’ve never subjected to anyone degrading you. Not without severe consequences in the end.”

“But I’m not that man anymore. I want this. I felt… alive…again.” Oswald tried explaining himself, “Earlier, when you were saying those terrible things. I- “ He paused again, mildly embarrassed, “I felt aroused.” Oswald ended it in a whisper.

You sucked at your lip, trying to ignore the thrill of excitement at his words. This wasn’t Oswald though, and while it had been fun to tease and taunt him earlier, you hadn’t realized to the extent he had changed. Emboldened by your silence, Oswald dropped to his feet, crawling forward to kiss your shoes. You jerked back, “Oswald no… I can’t. Not like this. There’s something I have to tell you.”

He looked up at you, pleading, “Please. It can wait. Mistress, please…”

Instead of accepting his request, you dropped to your knees. “Oswald. It can’t wait. They killed your father. They put drain cleaner in the liquor.”

Oswald started shaking, “No.. no they wouldn’t. Why would they do that?”

Placing your hand on his shoulder, you squeezed it gently, “It was meant for you. Just so you would never inherit your father’s estate. Oswald, I’m so sorry.”

Tears were pouring down his face as his body wracked with sobs and he fell into your arms. “Shh… it’ll be okay.” You comforted him, stroking his hair and trying to ignore how he was falling apart. “They’ll pay for this one day.”  
Oswald stilled, his sobs quieting into sniffles and he pulled away, wiping at his face. “They’ll pay today.” His voice was assured and you began to see that hard look flint into his eye. “I’m going to hurt them. Just like they hurt me…”  
There was nothing you could say to that. It was a relief in a way, seeing that glimmer of his former self emerging, blending into his new personality. He struggled to his feet, determination in his eye. Oswald straightened his clothes, smoothing out the creases and heading towards the door.

You stood, watching him leaving. A long sigh drew itself from your body and you slumped on the bed while you mentally prepared yourself for dinner.

X.x

Dinner was an amusing affair. Grace, Sacha and Charles were far more merry than they ought to be considering that Elijah had died not long ago. You avoided drinking the wine, choosing to stick to water. The food you merely moved about on the plate, hesitant to taste it until one of the others tried it first. It was safer, considering that Oswald was silently simmering. They made him stand in the corner, waiting for the flick of fingers to fill a wineglass or take away a plate. The Van Dahls hadn’t noticed the change yet, but you were acutely aware of it. The dark glint in his eyes, the tightening of his hand around the neck of the bottle as he watched them.

Excusing yourself early, you feigned a headache and retired. That’s when you heard the screams before they abruptly silenced one by one. Your heart was thundering, suddenly fearful. Was the Oswald you knew really back? Would he punish you for your words?

The door burst open, and Oswald stood there. The soft lighting of the room highlighted the glare of blood splattered across his face.

“I… I killed them.” His voice shook and he dropped to his knees. “I slaughtered them like animals.”

You hurried to him, wrapping your arms around his body as though that alone could reassure him. Slick warmth spread across your palms and you realized it was blood. He was covered in it. There was a mixed expression of horror and delight on his face. He licked his lips, tasting the coppery iron against his tongue as he stared at his hands. They shook, a jittery dance of adrenaline.

“Oswald, what you did was right. They deserved what they got. They killed in cold blood, just for an inheritance that doesn’t belong to them. They made you a slave to them, when you’re a king.”

He soaked in your words, letting them sooth his inner turmoil. “Thank you Mistress.” The term was chosen deliberately. Oswald felt the thrum of arousal burn through him, and he wanted this. He wanted your ownership, your guidance.  
Sensing his tone, you drew in a quick breath, “Oswald are you sure?”

The eyes that caught your gaze were certain, self assured in what he wanted. There was no hesitance left. Closing your eyes for a moment, you drew yourself back into that mindset. Where you were in charge, and Oswald was to bend to your every whim.

“You disgust me. Coming in here so filthy.” You suddenly snapped, and Oswald’s flash of excitement assured you. “I’m sorry Mistress.” He cowered before you, and you stood, snapping your fingers. “Come on. “

He struggled to rise and you made a noise of irritation, “Did I say you could stand? I have rules, Oswald. You must ask before you do anything.” Oswald relaxed back to the ground, peering up at you. “Mistress, may I please stand?”

You made him wait, tapping your foot thoughtfully, “Yes, you may. Now what do you want? What would you ask of your Mistress?”

Oswald was struggling with his words and you frowned sharply, “Mistress won’t give anything to you unless you ask.” The warning was enough to draw his words out.

“I want to be tied up.” Oswald whispered, he watched your face for a reaction, but you didn’t give him any. You were waiting patiently for him, “To a chair. I want to be blindfolded.Punished for what I’ve done. ”

His wants were clear enough, and you eyed the furniture in the room, selecting the hard wooden backed chair that was used for the vanity. “Sit.”

The command was firm and held no room for discussion. Not that there would be need for any, not with the way Oswald so eagerly limped to the chair, sitting with certainty and he waited with patience as you tied him up. The ropes scratched against his wrists, small flakes of dried blood pulling away and floating to the floor.

It was a macabre sight. Those bright luminous eyes looking up at you, expectant and timidly waiting for your harsh words to flay into him. The blood was dark against his skin, it’s ruby shine fading into a dull cooper as it began to crack across his face. His clothes were equally drenched and you breathed in the tangy smell of iron. It was sweet and rancid in the air, death enrobing him like a lover. Pulling his tie loose, you slipped it over his eyes, limiting his vision and Oswald’s nose flared. His other senses were sharpened, forcing themselves to be more aware of every move you made.

“Little Penguinella…. ”You choose the name from this morning, it’s cruel syllables resonating with him and his breathing quickened. Picking up the crop from your table, you stroked it across his shoulders, down his chest and caressing the noticeable bulge in his trousers. “Disgusting… so filthy and dirty…”

The words trailed on, each a sharp tap into his body as Oswald receding into the sensation of it all. The hard caress of your voice, the flicks of the crop against his body and the throbbing arousal that was his cock. This continues, he’s dancing between pleasure and pain. His clothes are opened, your hand stroking along his cock. Then you say something. He can’t recall quite what it was, but suddenly he was seeing those terrible visions from Arkham. His mother soothing him, and then he was bound like this, unable to speak, only watching as he bludgeoned his own mother to death.

Oswald is suddenly crying, a wordless scream tearing from his body as he pulls against the restraints. This isn’t a bit of play fun, this is him actually begging you to stop. Instantly you drop the crop, your hand pulling away from his weeping cock and your fingers are furiously pulling at the bonds. “Os.. Os darling, it’s okay. I promise. No one is going to hurt you. No more.”

“I can’t do this anymore.” He’s crying again, thick tears splashing down his face and you hate yourself. You can no longer recall exactly how many times you’ve held him like this now. Motherly and soft, cooing soothing words to him as he chants over and over again that it’s his fault. His fault that his mother died, his fault that his father died… murder and mayhem, and Oswald thinks he’s the cause.

It may be partially true, but it doesn’t mean he should carry that blame. His self hatred is flaring, and Oswald is begging once again to be beaten, as though taking penance out on his flesh will help. You know it won’t. There is nothing in you that will make you strike him again. Not like this.

Instead you take a firm upper hand on the situation. “Oswald, you may stand and walk to the bathroom.” He blinks slowly, absorbing the order and his grief slacks. The order is something he can do, something he can use to pull away from his poisonous thoughts.

He moves, and you following, directing him. Obeying every order, Oswald fills the tub with steaming water, adding in the bath mix. The soft aroma of vanilla, lavender and milk mixing into the water, creating a milky film. You waited patiently, giving him the softness he requires right now. There was so much loathing and self hate shimmering beneath the surface, and you don’t want to push it. Care and love is what is needed.

Letting him disrobe you, he joins you in the water and you lean back against him. He chooses to concentrate on providing pleasure to you, washing your body and massaging your shoulders. The soft contented sighs were music to his ears after the shrill wretched screaming of his… family. Oswald refused to think of that, pushing their horrified faces from his mind. His mother’s face still drifts in and out of his thoughts, his father’s smile. He faintly wonders if they’re together again, ghosts that mill about, finding the other in death.

It was with gentleness that you turned in the tub, the water splashing up along the sides as you straddled him. Every movement was chosen carefully, from the delicate touch of your hand against his face as you softened the caked blood and picked up a cloth to wipe it away, to the way you kissed him. The sweetness of your lips against his had Oswald forgetting his torments. They burned away at your touch, Venus amongst men, the reddened droplets of water sliding over your skin. Looking down at the bathwater, he marvelled at the rust tinge of it all, his hands stroking through it, creating ripples and waves. Finally he was unable to ignore his needs, your hands were everywhere on him, but where he really desired them to be. Oswald kissed the backs of your knuckles before immersing your hand in the water and encircling your fist around his cock once more. It came to life, eager and intent as his mouth found yours again. A breath of life coursing through his lungs as he drew against yours. Feverously he helped guide you onto his length, letting you sink down on him with a satisfied sigh. He was finding sanctuary perhaps, a place deep within you that called to him, drawing him further in.

The water rocked against the sides of the tub as you rode him hard, the red tinged liquid splashing to the floor and disappearing against the dark tile. His hands curled over your hips, guiding you, coaxing you on. There was a sharp predatory gaze in the bright eyes that met yours. His mouth opened, teeth bared and they sunk against the skin of your shoulder causing you to cry out. The indents of his teeth on your flesh would bruise, but he kissed it lightly, barely brushing over the damaged tissue.

Your hands are clenched against his hair, tugging as your orgasm washes over you. The walls of your body clamping down on him, and Oswald’s mouth is open in a panting cry as he finally lets go. He lets go of more than just his release. He lets go of that part of himself that simpered and catered to people who abused him. He lets go of his fear, his self hate, and his voracious craving for acceptance.

He strips those pieces of himself, leaving them behind in the dirty bathwater. Oswald Cobblepot is reborn.


	25. Demented (masturbation)

Oswald leaned back in his chair, the heady taste of cooper and wine mixing in his mouth as he stared at the corpse of his dearly departed step-mother.

A real fairytale ending, he thought darkly. The crystal wine glass was cold in his hands, unlike the warmth of the blood that was beginning to settle against his skin. His tongue darted out, capturing the last droplets that escaped his lips. His hunger was not sated. There was an itch under his skin, a reawakening of the man he used to be. Perhaps he would never be that man again, but now he was better. Unhinged, some might say, but he was ruthless. The only weakness in his bones was the familiar ache of his leg, the reminder of what had begun his descent into the hellish world he lived in.

A low laugh rumbled in his chest, “Oh Grace…” Oswald made a patronizing noise. “You thought you could fuck with me…”

The sharp cruel tones of his voice rang high and echoed about the dining room. The thrum of adrenaline and excitement still filled his veins, and Oswald gently chewed on the inside of his mouth, hand stroking down his suit. It was stained, splattered in her blood. But no matter. It was a memento. He’d keep it exactly how it was. A piece of his father, and the retribution Oswald had wrought about this…. Oswald couldn’t decide on a fitting word. She was filth, dirty scheming filth. He really ought to have dragged out her punishment. Charles and Sacha had been but mere cruel mocking children. A echo of the abuse he’d suffered as a child.

Arousal was pooling in his crotch, a familiar tug that he’d missed. A fiendish approach perhaps, but Oswald had always felt so… alive… after a murder. This wouldn’t be the first time he jerked himself off in cold blood.

A sickening satisfaction filled him as he took his length in hand, the slick of his blood covered palm against his cock was euphoric. Oswald’s breathing became more erratic as he tossed himself, eyes centered on Grace’s slackened face. The curving smile the knife had made against her neck. Nose flared and Oswald breathed in deep the aroma of the room. Death, a rancid coppery musk that elated his senses, flooding them with all the times he’d spilled it.

It was beautiful after all. Those ruby red drops, spreading into pools of sticky liquid beneath her. Sickly bitter to taste, but such a sweet entree in the end. He continues to pump his hand over his length, thumb rolling over the head as the smear of blood mixed with the opaque liquid dribbling from him.

Fuck, all he ever wanted was a little respect. And now here he was, vile and disgusting, jerking himself off in front of his dead step mother. But right now, he wouldn’t have it any other way. Revenge was delicious he thought, as his body shuddered, cock twitching in hand as it spurted ropes of cum against the table.

“Oh Grace, I hope you’ll clean up. I do hate a mess.” Oswald sneered at the corpse, following it with laughter that bellowed and grew. A madness filling the house, soaking into the very fibre of it. A house of darkness and horror. A birthplace of demented demons.

How apt, he thought zipping himself away. This house would have many ghosts now. He had made sure of that.


	26. Hold Me Down (Facefuck)

My demons are begging me to open up my mouth

The only demons lurking inside your body were the ones hungry for flesh against flesh. For the electric touch that had you panting, begging, screaming for him.

I need them mechanically make the words come out

They were always pushing, slithering under your skin and pestering you. Ask him. Better yet, beg him. He liked it when you begged. You could always see it in his eyes, how your frantic need for him excited him, drew him to you. The thought that he could bring about these feelings, these irking needs that plagued you until you were a desperate mess pleading with him to fuck you.

They fight me, vigorous and angry, watch them pounce

Only he could sate your desires. His bright eyes full of mischief and that glint of knowing. You were always wet for him, your thighs slick against each other with evidence of your arousal. How desperately you needed him, you only ever felt truly complete in his embrace.

Ignite me, licking at the flames they bring about

Only he could quench your hungry fire. His light fingers tracing over your body, a familiar pathway across your curves soothing you. Sometime’s he’d press you hard against walls, leaving bruises across your skin, small reminders that you’d smile at in the mirror. Always you were eager for his touch. On occasion it would be soft, his lips brushing over collarbones, those stands of black hair tickling across your skin. He would follow down the lines of your body, slipping between your legs and eliciting such a chorus of sounds from you with his tongue alone.

I sold my soul to a three-piece

And gods he was beautiful. Unconventional in his sharp looks, with that bird like shape of his nose, but that was easy to love. Especially when he looked at you the way he did, with those bright seafoam green eyes and mess of perfectly sculpted bangs across his brow. Even the way he carried himself. …

And he told me I was holy

He was a man who knew how to worship. Perhaps all those Sundays where his mother took him to church, reminding him to confess his sins, were to thank. Those clever words soothing and coaxing, uttering up offerings as sweet as honey. After that first night, it hadn’t taken much to convince you that he was the only one you’d ever need. You’d come begging to him, your skin feeling tight and uncomfortable without his against it. He’d studied you curiously, surprised at your need but he flicked his fingers out, signalling his men to leave before he ravaged you against the table,

Tonight was much like that one, except it was in a mansion of ghosts and he reigned from a blood stained chair.

He’s got me down on both knees

“I want you to face fuck me.”

The words trembled in the air, and Oswald held his eagerness back, letting it simmer beneath the surface. You were always more receptive to his touches after being left wanting.  
“Now?” He raised an eyebrow.

You sucked your bottom lip in, teeth stark white against them, biting at the plump flesh. “Please, I.. I want to taste your cock.”

He nodded thoughtfully and gestured for you to get on your knees in front of him. Leaning forward Oswald studied your face, taking in the excitement evident in your eyes, the flush creeping along your skin, and the shiver of anticipation that followed. Your gaze followed his hand as he raised it to stroke his knuckles against the curve of your cheek, sliding down to cup your chin lightly.

Those fingers brushed along your lips and you opened them willingly, tongue flattening out and teasing against your bottom lip as you looked up to him. He loved you on your knees, a proper worship of the ruling King he was.  
He would rule your body, have you at his back and call. You relished in it, the idea of Oswald commanding you, using your body to his pleasure.

Oswald gripped your hair tight, his fingers threading through the strands, the colour stark against his pale skin. He tugged, pulling against your scalp roughly and you moaned.

“That’s my girl.” He smirked, leaning back and spreading his legs wide to accommodate you shuffling closer to nuzzle against his crotch.

Selfish, taking what I want and call it mine

Your own body thrummed with need and want, your fingers itching to sneak beneath your clothes, but you restrained. You wanted this to be about him first. You let your trembling fingers reach for the fastening of his trousers, the expensive italian fabric rich against your hands. Oswald did nothing to help you, merely watching with thinly veiled interest as you opened his pants, coaxing them down his hips, revealing the patterns socks with leg garters. The trousers created a dark pool of fabric on the floor, but you were already pulling at the band of his underwear, pulling that away to reveal your prize.

He was already at half mast, his body intrigued by your proposition. You grasped the base, tongue flicking out and tasting him. Soon he was hard and slick, your saliva coating along his skin, the head weeping opaque tears of precum and Oswald was lightly stroking his chair as he watched you finally open your mouth to take him in.

That’s when he moved.

I’m helpless, clinging to a little bit of spine

Oswald curled his hand possessively over the back of your head, forcing you down to meet his thrusting hips. Choking and gagging around his cock as it pressed against the back of your throat, you tried to relax, to adjust to his size with your eyes watering. The constant pressure on you was dizzying, his touch firm as he held you down, guiding your head back and forth on him. Sloppy wet gagging sounds filled the room, mixed with the creak of the chair and Oswald’s quiet grunts. Finally he released you, letting you pull away, strands of spittle connecting you still. Streaks of your makeup ran down your face, lips plump and reddened from their abuse.

They rush me, telling me I’m running out of time

Gasping breaths were drawn in, reminding you that you needed oxygen to live. You felt light headed, floating in your ecstasy of being used. Opaque fluids trailed from your mouth, smearing across your face and Oswald smirked, letting you have those sharp breaths before he filled your mouth again. His hips jerked, quick and erratic in their rhythm. At last he put pressure on you again, this time easier for you to relax your throat and let him push you down, your nose brushing against his groin and Oswald stilled suddenly, hot spurts of cum filling your throat and he pulled out, his hand making quick jerking movements to milk the last of his seed across your face.

Obediently you swallowed, opening your mouth to receive his gift, the final shots landing over your lips, cheeks and breasts. Oswald let himself relax back into the chair, the bliss of his orgasm fading.

They shush me (shhh), walking me across a fragile line

Tired, jaw sore, but you were oh so pleased with yourself. You slumped, leaning against his leg and resting your head on his knee as you collected your bearings again, the ache of your own arousal almost impossible to ignore. Oswald gently brushed his hand over your head, like a good pet he kept. “I’ll take care of you soon, my dear.” Oswald murmured, looking at you with fondness.


	27. Ruffled Feathers (couch sex)

**Summary for the Chapter:**

> Prompt: Couchsex, markings Oz & Reader on the couch where it’s pretty rough sex and he leaves a lot of hickeys all over her, and she leaves deep scratch marks down his back as he fucks her?

You were lying across the couch, contently reading when Oswald come home. Glancing up you smiled at him briefly before returning to your novel. He shrugged his suit jacket off, rolling the cuffs on his shirt up and tugged the cravat free before popping the first buttons on his collar.

“Do you want a drink?” He offered, already pouring a glass of wine for himself. “No… I’m alright.” You called out and deft fingers flipped the pages, eager for the next chapter. Oswald leaned against the door, watching you with amusement. He certainly could see why you were more engrossed in your literature instead of him. The cover was of a overly buff man, probably covered in oil based on how glistening his flexed muscles looked and a woman in his arms. A sly smirk came to Oswald’s lips.

Hobbing over, he took a seat, lifting your feet to place them in his lap. Subtlety he began massaging your feet, seeking out the pressure points that made you bit your lip and hide a moan of pleasure. Placing one down, he collected your other foot and you glanced over your book at him. He was watching you intently, and a quick devious smile came to his lips when you caught his eye.

Slowly, Oswald lifted your foot, placing a kiss upon your ankle. His gaze was smoldering, lips touching down onto your skin as he created a trail up your calf. Teeth nipped lightly at the inside of your knee and you gasped. Your book dropped to the ground, forgotten in favour of a far more tantalizing offer.

Fingers trailed over skin, stroking up the curve of your thighs to reach the sleep shorts you work. Raising your hips to let Oswald tug them down, he teased kissing back up your legs, avoiding the spot you needed him to touch the most. Those lips brushed over your hips, fingers digging into the flesh light as he squeezed and pulled you closer. You could feel the bulge of his trousers pressing against your core.

He rocked into you, hips grinding against you firmly as he captured your lips in a rough kiss. Oswald ran his hand through your hair, closing his fist and tugging. The moment you opened your mouth in a gasp, his tongue slid in. He tasted of wine, bitter and heady all at once.

Hands were busy pulling at his clothes, and Oswald barely took time to pull back in order to shrug them off and toss them to the floor. He was quick to tug your t-shirt over your head and toss it. It landed on the lamp, dimming the limited light in the room even more.

Oswald took to marking your exposed skin, teeth scraping, biting down, sucking against the skin until you couldn’t stand it. He relished in the whimpers and encouraging cries. The way your fingers bit into his skin, and you arched in his grasp. Bruises blossomed like roses over you, claiming you as his own. Nothing about his actions were soft, nor sweet. He was owning you, making you his over and over again until you were begging. Your body strung high, desperate for release when he teased you with his lips, his touch against your body.

“Why my little dove… you are so very wet for me.” Oswald whispered against your lips, finally drawing back up your body to kiss you once more. His fingers were sliding against your cunt, teasing your clit lightly. You gasped, the muscles of your thighs quivering. “Oh god… just fuck me already.” The pleading cry fell from you and Oswald certainly wasn’t going to say no. Not when your nails scraped across his scalp, ruffling his hair and if anything making him even harder.

Rolling a condom on, Oswald glanced up at you quickly before he grasped the base of his cock to guide it into your slick center. “Shit…” He hissed, relishing in how wet you were for him. How your cunt welcomed him so easily.  
Oswald grunted as your nails scraped down his back, and sharp stings of pleasure ignited within him. “Again.” He demanded, and groaned as you repeated the action with glee. He shifted, pushing your legs over his shoulder so he could get a deeper angle and you cried out, tossing your head back against the couch. Pleasure was building, a tingling intensity within you that was about to break.

He could always tell. The way your eyes glazed, fingers digging into him and toes beginning to curl. Oswald manoeuvred a hand to rub your clit and then you broke for him. Cunt pulsating around his cock as he fucked you through your orgasm. You were calling out his name, deep breathless gasps mixed with those familiar syllables. “Oswald!”

Giving one last hard thrust, Oswald came, a shudder running through his body. Hands gripped tight over your legs and you watched as his eyes closed shut, mouth dropping open. His hips gave a few last lazy rolls, pumping his cock into your sweet heat. “Ahhh….” Slowly he came back to himself, green eyes fluttering open and looking down on you with bliss.

The pair of you relaxed. Your thighs tingling in protest and relief at being let down, and he settled between your legs. His head rested against your chest, listening to the quick beat of your heart.

“I love you.” Oswald murmured, tilting his head to press a kiss to your sternum tenderly. You smiled, heavy with satisfaction. “I know.” Your fingers combed softly through his hair, soothing out the tussled locks from before. He sighed happily, tightening his grip around your waist.


	28. Stay With Me (comfort sex)

**Summary for the Chapter:**

> -(Female) reader had a bad day and just wants to be in bed with him for the rest of the night

The blankets on the bed weren’t enough. They gave enough weight to be only mildly comforting, a shield of sorts against the miserableness of the day. You curled into bed, hugging your pillow close and wishing it was your boyfriend Oswald. For whatever reason, today nothing seemed right in the world.

It gnawed at the bank of your mind, preying on your insecurities and you chewed on your bottom lip. Oswald’s voice broke you from your concentration, the repeated track of everything wrong that had happened.

“Dove? What’s wrong?”

Even his pet name, that usually lifted your heart, did nothing but put the faintest of quirks to your lips. A sad attempt at a smile when he leaned over the bed, balancing one hand at your side and stroking the other over your temple. Worry was in his aquamarine eyes. “Hey.” You murmured, reaching to cover the hand he was using to balance with your own.

“Just a bad day… Os… will you stay in bed with me? I don’t feel like going out.”

You knew he had arranged dinner out at a fancy new restaurant he was eager to try, and you felt awful for asking him to change his plans. But it felt like your limbs were filled with sand, heavy and unyielding. You didn’t want to go out, to put on that cheery fake smile and act like nothing was amiss.

Oswald nodded, leaning in to brush a kiss to your forehead. “I’ll be back momentarily my dear.”

The mattress lightened as he got to his feet and you could hear his uneven step and the soft closure of the door. There was a quiet murmur of voices and then Oswald was back. He carefully untied his shoes, setting them away and shedding the rest of his suit in favour of a tee-shirt and pajama bottoms.

Pulling the covers back, Oswald slipped in beside you and immediately you melted into his arms. Clinging to him like a lifeline. One leg hiked over his hip and pressing your face into the crook of his neck. His warm touch soothed over your body. Oswald was holding you close and breathing in your scent. Gently he rubbed comforting circles over your back, whispering how much he loved you.

You were beautiful. Wonderful. His dove, his world, his everything. He tilted your face up, lightly brushing his lips over your own before gently capturing them into a deeper kiss. One that made you forget your worries. All that matter was how he was making you feel. Loved. Safe.

His hands were stroking over your ribcage, thumbs brushing lightly over the underside of your breasts before moving on, following the curve of your waist and running over your ass, pausing briefly to squeeze and then they continued. Oswald stroked over your thigh, tucking under your knee and pulling you impossibly closer. “I love you.” Oswald pulled back from his kisses, and you caught your breath. Already your body was beginning to hum with arousal. His words only added to it. Affirmation of his affection, his desire, his loyalty to you.

You guided his hand to the apex of your thighs, slipping it under the waistband of your sleep shorts and Oswald swallowed quickly as he felt how wet your lower lips were becoming. His fingers parted them, an index finger sliding along your folds, spreading the juices and gliding over the tight bud of nerves that made up your clit.

Already you were rocking into his touch, lip tugged between teeth, never breaking your gaze. Oswald loved watching your expressions as he pleasured you. They drifted over your features, sometimes lingering when he worked his fingers in a particularly pleasing way, while others flashed by, quickly replaced with ones of desperation when he held off. It was a slowly building crescendo, accented by the soft moans and cries that rose from you. Oswald kissed them away, stealing them from your very lips. He drank you in while the pads of his fingers wrought pleasure from your swollen sex.

“Os…” You broke away, letting out a long pleasured sigh when he finally slipped two fingers into you, pumping them at a remarkably lazy pace. It was holding you on the edge, making you dangle over the abyss as he watched with sharp eyes. Oswald knew your body so well, making it his sole mission to discover every sound of bliss he could pull from your body with his touch.

Finally you were about ready to beg, desperation showing behind your eyes as you clasped fingers tightly over his wrist, hips rocking against his hand and Oswald hid a smirk. “That’s it dove… cum for me.”

Your fingers threaded through his hair, closing and tugging him into you to kiss him deeply as your orgasm wrecked through your body. Your thighs quivered around him, the walls of your pussy milking his fingers and he groaned into your mouth, tongue playing against your own as he felt you clamp down on his digits.

Finally the waves of pleasure passed, leaving your body blissed out and relaxed. Oswald slipped his hand out of your shorts and they settled back with a soft snap against your skin. His fingers were drenched, glistening with your juices and you moaned when he put them in his mouth to suck them clean. “You taste so good darling… “ Oswald promised you, finally releasing his own hand once his tongue had licked away every lingering taste of you, leaving only saliva coated digits. “Feeling better?”

You nodded and kissed him again, this time sensing the taste of yourself in his mouth and Oswald hummed in response. “Thank you.”

“You’re welcome.” He lay back against the bed, and you tucked into his side naturally. “Get some rest, Schatz…” The German endearment rolled off his tongue with remembered ease and you both closed your eyes, content in the comforting aftermath of your evening.


	29. Entertainment (threesome w/Edward)

**Summary for the Chapter:**

> Prompt: Maybe like, after Ed gets out of Arkham he goes to live at Oswald’s, where the reader is also residing as a live-in maid/servant/assassin? Something like that. Leading to smutty goodness (maybe some peanut butter involved too? You started a thing with PB for me thanks) xoxo

It was frustrating… these last couple months living with Oswald. You were both his hitman and his lover. Yet lately, neither of which seemed to interest him. He’d announced his bid for Mayor of Gotham and since then had no time for anything else. Not even you. Too often he was brisk, coming to bed late, and leaving early. There were some evenings you didn’t see him at all. He’d lock himself away in his office with Edward, going over speeches and plans…

Well enough was enough.

Giving yourself one last glance over your reflection, you smirked. How could he resist this? Oswald’s favourite set of lingerie. Deep purple lace bra that revealed perky nipples, crisscrossing straps over your waist that lead down to the garter belt holding up black sheer stockings. And then the panties…. Indecent revealing lace that hugged your bum. He’d bought it for you, insisting you model it about the bedroom as he sat and sipped his wine. Now that had been a good evening. Crawling into his lap, Oswald’s expression of eagerness as he shoved aside your panties to fill you deep… The wine soaked kisses and gasping moans as you each brought the other over the edge of pleasure.

Slipping on Oswald’s fur collared coat, you breathed in his scent. Musky expensive cologne and slowly you opened your eyes. Already your pussy was getting wet, just at the thought of how he’d tug the coat from your shoulders, kiss up your wrists… maybe he’d twist them behind your back and his hand would caress your ass before slapping it. A mixture of pleasure and pain that always had you begging for him.

His gloves were there as well and you tried them on, trailing them over your body. If you closed your eyes, you could almost imagine it was Oswald’s hands rolling your nipples between his fingers. But then the clock chimed, breaking your daydream and a smile graced your lips.

Oswald would be home soon, and you would wait in his office. Sliding on your heels, you hurried down the hallway and snuck into his office to arrange yourself across his chair. The coat was barely closed over your waist, and your legs hung over the side of his chair as you sat on it sideways. It was tempting to pour a thimble of scotch to sooth your eager nerves, but already you could hear Oswald’s voice down the hallway.

The door opened and he walked in, Edward by his side as always. Oswald didn’t notice you at first, but his friend did. The taller man’s eyebrows rose and there was a sharp smile of appreciation as he appraised your appearance. Immediately you swung your legs down, tugging Oswald’s coat closed to cover your thighs.

Edward cleared his throat, interrupting Oswald and nodding towards you. Your boss turned and frowned. “What are you doing?” His temper was short today and immediately your pleasant seductive smile faded.

“I thought we’d have a private evening together.”

Oswald waved off your words. “I don’t have time for that. I have work to do.” He waited for you to rise from his chair before he took it. “Edward, could you escort her out and take care of her. Entertain her… or something. Since she’s incapable of doing it herself.” His snark hurt, and you glared at him. Incapable of entertaining yourself… hah…. Like you hadn’t already been mastrubating with his name on your lips for weeks.

“Fine.” You muttered, pushing past both of the men. Edward followed you out, staying close like a shadow. There was silence between both of you, just the soft muffled sound of your footsteps against the carpets that lined the hallways.

There was a short tug on your elbow and you turned to Edward in confusion. There wasn’t much time though, not when he pulled you into a supply cupboard and closed the door behind him.

“What do you think you’re doing!?” The demand was there and you tried to glare at him. However it was dark, with only the sliver of light coming through the crack of the doorway. He invaded your space, forcing you between the shelves holding pressed linens and silverware and his firm body.

“He said to entertain you…. Don’t you want to be entertained?” Edward’s voice was husky and soft, half lidded eyes looking down on you. His fingers drifted to your coat and you dropped your hands away, just to see what he was going to do. There was no denying that Edward Nygma was an attractive man. With his dark eyes and occasionally sinful grin. Especially now, when those large palms of his slipped inside your coat and stroked across the straps from your set. His hands were warm, touch firm and steady.

You swallowed, breathing softly through your mouth as he leaned down. He didn’t kiss your lips. Instead his attention was on your skin, mouth brushing over your collarbone and pressing dry kisses further down your chest. Teeth grazed across your pert nipples through the lace and you raised your gloved hand to your mouth to stifle the gently moan of pleasure.

There was no doubt about it. This made was certainly making you wet, and pudding under his touch.

And he knew it.

Edward knelt, looking up at you to catch your eye as he turned to kiss your thigh, just above the embroidered lace stocking tops. He was teasing you. Kissing just up to the apex of your thighs and then back down. Thumbs rubbing reassuring circles against the bare skin as he stroked over the curve of your ass. He nuzzled his nose to your panties, breathing in your arousal and flashing a wolfish grin.

“Don’t be such a tease…” The words you breathed only made him pause with his thumbs looped under the waistband of your panties.

Edward hummed, sliding them down your legs and letting you step out. “But where’s the fun in that?” He commented, drawing one of your legs over his shoulder. You leaned back against the shelving, balancing carefully as he delved in, licking a slow stripe up your womanhood.

God’s it felt good. His long tongue slipping between your folds to flick over your clit. Instantly you bit at your lip, holding back every keening cry that he was prepared to drag from your body. Fingers joined, slipping into you and curling to find your g-spot. Edward gripped at your thigh with his spare hand, pleased by the quiver that trembled through your body and then the shudder as you came. He lapped at your juices, tongue tentatively running over your pearl again. It drew a sharp gasp and your finger tangled in his hair. It was too much. Too sensitive and yet so perfect. Edward put his mouth back to work, forcing another orgasm to rush through your body. Everything tingled, and you couldn’t form coherent words. Just held his face in place and tried not to rock your hips against him as he brought wave over wave of pleasure.

When he finally pulled away, Edward looked smug, your juices glistening over his mouth and chin. “How was that for entertainment?” Edward asked coyly, tugging a handkerchief from his pocket to clean himself up. You were sagged against the shelving, holding onto it as you didn’t trust your legs to bear your full weight.

“Not bad..” Each word was breathless and you grinned at him, alight with mischief in your eyes, “… for a pre-show.”

Edward licked at his lips and smirked. “Why don’t we move this to my bedroom then?”

There was little guilt as you followed him into his bedroom. After all…. If Oswald wasn’t going to bother to appreciate you, then why not let Edward?

x.x.x

Oswald couldn’t sleep. He had been attempting to change his sleep schedule to be more accommodating to the business of being mayor, but years of living the nightlife and conducting business during dark left him restless. Plus he didn’t know where Edward had disappeared to. A short text had been sent by his friend. Stating he was retiring for the evening, bemoaning a headache. Oswald could sympathize. The campaign had been grueling to date and he worried that he was going to lose his winning streak. They were so close…

And you… Oswald had no doubt where you were. Probably in your room, sulking over his dismissal. He knew he should pay you more attention, otherwise you would go wandering, like a minx who sauntered over to the neighbour’s house for milk. But Oswald simple wouldn’t put aside his thirst for power to spend it between those beautiful thighs of yours. Even this knowledge was keeping him awake. Oswald briefly considered making a visit to your rooms, but he would no doubt be rebuffed simply out of spite. He frowned.

Perhaps a snack would settle him. The temptation of food was enough to make him decide.

A long slow sigh escaped from Oswald’s lungs and he sat up, turning the covers back and swinging his feet over. He forewent the cane that rested beside his bed, it would be just a short walk downstairs to the kitchen.  
The walk down was uneventful, he nodded to the security guard standing by the front door of the mansion, but otherwise continued on his way. The kitchen was silent and empty, except for the opening of drawers and the cupboard. Oswald was intent on collecting a jar of peanut butter and a spoon. He hugged it to him, the lid already twisting away and the spoon dipping in. The first taste made his mouth water and Oswald sucked on the spoon, enjoying the salty creamed butter. Already he was wandering back to his room, slowly taking the stairs and then the ever familiar hallway back to his master bedroom.

A sound made him pause just outside Edward’s room. He was staying in one of the guest rooms, and the door was cracked just enough for Oswald to hear a soft breathy moan.  
“Edward…”

Oswald’s ankle gave way and he lost balance briefly. To steady himself he mistakenly raised his hand to use the door as a crutch, but instead it swung inwards, and Oswald stumbled forward.  
“Oh my…” He blinked rapidly, the spoon falling from his hand and clattering against the floor.

His friend was mostly naked, glasses slightly crooked on his nose. The only remaining article of clothes was his trousers that were open and slung low on his hips. Edward stared back at him, but Oswald didn’t notice at first. He was far more concentrated on the fact that his assassin was on her knees in front of Edward and had his friend’s hard member in her hand.

“Hi boss…” You looked unsure, trying to gauge your lover’s shocked reaction. “Care to join us?” Edward added in quickly, pushing his glasses back up his nose.

Immediately Oswald shot a look at Edward, “I did not mean…THIS… when I said entertain her.”

He couldn’t decide if he was furious or aroused. He had never explicitly stated that you would be exclusive… but he hadn’t expected to be confronted with this.

You rose from your knees, sauntering towards Oswald with a sensual sway to your hips. He took note of your lingerie, the panties still missing and your sex bared to him. “You had to wear that set for him?” There was accusation in his tone and you pouted.

“I wore it for you under your coat… Mayor Cobblepot… but you shooed me out before I could undress for you.” There was steel in your words and he felt conflicted. Seeing his hesitance, you dropped down in front of him and gently pulled the jar of peanut butter from his grasp. Swiping a finger through it, you opened your mouth and looked up at him as you began gently bobbing your head over the coated digit.

His pulse raced and Oswald could feel his slacks tightening as his cock twitched and grew. It was so easy to imagine that it was his cock you were licking and sucking on with such enthusiasm.

Edward skirted around the pair of you, running his hands over Oswald’s shoulders and leaning in to whisper. “Doesn’t she look good on her knees. All desperate and hungry for your thick cock…” The words were just the beginnings of the filth that would drip from his friend’s mouth. Oswald let him open his robe, drawing it from his shoulders, much like he had done with Oswald’s coat from your body earlier.

Eager hands pushed Oswald’s pajama pants down and he fisted his cock, bringing it to hardness. A groan escaped his lips as you replaced his hand with yours, licking one long stripe up the underside of his shaft before taking him in your mouth tortuously slow. Edward was opening Oswald’s shirt, then tossing it aside. He kissed Oswald’s neck, reaching around the man to stroke up his body and play with his nipples.

Immediately the mayor to be was putty in their hands. Hazy cerulean eyes opened, their pupils blown wide with arousal. Oswald had to clear his throat, “Alright. I’ll join you.”

You pulled away with a popping sound, releasing his dick and rising to your feet. “Let’s have some fun then?” Your bra snapped open and you dropped it to the floor. Both men’s eyes were on you, dark and ready. Taking the peanut butter you carefully drew it through the valley of your breasts and encircled your nipples.

“Why don’t you come eat, Penguin?” The suggestion was irresistible. Especially when you backed away, arranging yourself across the covers of Edward’s bed and painted another trail of his favourite treat down your naval.

Oswald followed, crawling up the bed and settling between your legs to lick and kiss the delightful path you’d left for him. Your hands stroked through his hair, tightening and pulling slightly as he nipped down lightly on one nipple to draw a keening cry from your plump lips. Gaze drifting from Oswald to Edward, you watched him, biting at you lip and tugging it between your teeth. He had slipped the last of his clothes off and was lazily stroking his cock in hand as he watched you.

It wasn’t long before Oswald had cleared away every trace of peanut butter and was now sloppily kissing up the column of your neck before capturing your lips. Tongues slid against each other, and you could taste the nutty flavour on him.  
He was drawing quiet moans from you, and you could feel the bed compress as Edward joined. Long fingers trailing over your body, drawing you to sit up between the two men. Oswald at your front, Edward close behind you, letting you lean into his frame as Oswald played with your breasts, kissing and nipping at your exposed throat.

You could feel Edward’s erection press against your back and you drifted one hand behind you to circle around it, giving a few firm strokes when he bit down on your shoulder. “Edward…” His name came out as a sigh, and Oswald pulled away to watch. There was a hint of jealousy, and Edward recognised it. He whispered in your ear, “Please him first…”

It would be good to keep Oswald happy. Both of you depended on it.

So you pushed Oswald onto his back, straddling him and rising up just enough to guide his cock inside of you slowly. He stretched you and you gasped lightly as you slid down. The pace was slow, hips rocking and grinding down on him. Edward was behind you still, kissing your exposed skin and playing with the stockings still covering your legs. He couldn’t wait to have you bent over, his cock buried in you and fingers clenched around you garter belt to guide your movements. But first, Oswald had to have his pleasure.

Edward could wait, he was patient. His friend wouldn’t last long, not with the sharp breaths he gave and the flush creeping across his chest. Oswald bit at his lip, face screwing up as he spilled, gripping your hips to hold you in place, as he thrust up into you and shuddered.

Your hands splayed over Oswald’s chest, panting slightly as you felt him soften and Edward’s hands were impatiently on your hips, drawing you onto your knees above Oswald. Your boss brushed his thumb over your lips, looking far more relaxed and at ease then he had before. He rose up slightly to kiss you, silencing the moan as Edward pressed in suddenly from behind.

The lanky man sighed, you were so wet, your walls slick with Oswald’s cum still and he was going to fuck it out of you. His hands gripped the garter belt around your waist, tugging you back onto his cock, bottoming out inside of you.  
“Fuck… “ Edward grunted, his hips picking up a rough pace. He’d been waiting too long. First the cupboard and then all the taunting and teasing before Oswald arrived. Edward needed this. He needed his release. Your pussy was clenching around him, soft cries being stifled by Oswald’s lips as the future Mayor continued to kiss you hungrily.

The sensations were beginning to overwhelm you. Edward filling you so completely from behind, slamming into you with a harsh rhythm, while Oswald was beneath you. Your lover was claiming your lips, stealing away every breathless gasp and his fingers were rubbing against your clit. It pushed you over, dragging a shuddering intense orgasm through you.

Edward didn’t last through it. He pulled out, leaning back on his elbow and tossing his cock with two quick tugs before he spilled hot ropes of cum against his stomach. You collapsed next to Oswald, curving into him instinctively. Edward crawled over to join your other side, creating a sweaty cuddling mess. He nipped affectionately at your shoulder, glancing over to Oswald to gauge his reaction.

“Now that’s what I call entertainment.” You teased, entangling your fingers with Oswald’s as you turned to brush a soft tender kiss to Edward. Oswald watched this in silence, his thumb stroking over the back of your hand.  
He had to admit. This was certainly the best of both. He valued each of you a great deal, and knowing that if you were going to stay from neglect it would be to Edward…. At least he could control that. 

“Is this alright Oswald?” Edward drew away from your kiss to look closely at his friend. He adjusted his glasses, askew on his nose. He was getting better at reading Oswald, knowing how easily the man’s mood swung.  
It helped that you immediately cuddled into Oswald, pressing a kiss to his collarbone before looking up at him with attentiveness. “Yes…” Oswald began, glancing down at you before holding Edward’s gaze. “I don’t see why this couldn’t continue.”

Your smirk lit up your face. Entertainment indeed. This night was full of surprises.


End file.
